Structure

Physi-Chem Properties

Molecular Weight:  379.18
Volume:  391.284
LogP:  3.527
LogD:  3.176
LogS:  -4.801
# Rotatable Bonds:  3
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.697
Synthetic Accessibility Score:  3.262
Fsp3:  0.391
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.003
MDCK Permeability:  4.056989564560354e-05
Pgp-inhibitor:  0.951
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.094
30% Bioavailability (F30%):  0.375

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.975
Plasma Protein Binding (PPB):  77.07634735107422%
Volume Distribution (VD):  1.696
Pgp-substrate:  9.216736793518066%

ADMET: Metabolism

CYP1A2-inhibitor:  0.544
CYP1A2-substrate:  0.967
CYP2C19-inhibitor:  0.056
CYP2C19-substrate:  0.942
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.817
CYP2D6-inhibitor:  0.971
CYP2D6-substrate:  0.913
CYP3A4-inhibitor:  0.021
CYP3A4-substrate:  0.809

ADMET: Excretion

Clearance (CL):  7.588
Half-life (T1/2):  0.196

ADMET: Toxicity

hERG Blockers:  0.32
Human Hepatotoxicity (H-HT):  0.278
Drug-inuced Liver Injury (DILI):  0.946
AMES Toxicity:  0.789
Rat Oral Acute Toxicity:  0.594
Maximum Recommended Daily Dose:  0.906
Skin Sensitization:  0.923
Carcinogencity:  0.091
Eye Corrosion:  0.003
Eye Irritation:  0.025
Respiratory Toxicity:  0.941

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC233650

Natural Product ID:  NPC233650
Common Name*:   Tylophorinine
IUPAC Name:   (13aS,14R)-3,6,7-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-14-ol
Synonyms:   Tylophorinine
Standard InCHIKey:  LAWAARLALKUFQQ-CVDCTZTESA-N
Standard InCHI:  InChI=1S/C23H25NO4/c1-26-13-6-7-14-15(9-13)16-10-20(27-2)21(28-3)11-17(16)18-12-24-8-4-5-19(24)23(25)22(14)18/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23-/m0/s1
SMILES:  COc1ccc2c(c1)c1cc(OC)c(cc1c1c2[C@@H](O)[C@@H]2CCCN2C1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL398325
PubChem CID:   264751
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives
        • [CHEMONTID:0001906] Phenanthroindolizidines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5977 Tylophora crebriflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29040 Tylophora mollissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7170 Tylophora ovata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24049 Tylophora floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24049 Tylophora floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5977 Tylophora crebriflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7170 Tylophora ovata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29040 Tylophora mollissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5977 Tylophora crebriflora Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24049 Tylophora floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29040 Tylophora mollissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18435 Tylophora atrofolliculata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24043 Tylophora asthmatica Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens GI50 = 20.0 nM PMID[572883]
NPT461 Cell Line PANC-1 Homo sapiens GI50 = 11.0 nM PMID[572883]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 40.36 nM PMID[572884]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 20.14 nM PMID[572884]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 59.43 nM PMID[572884]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 56.75 nM PMID[572884]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 59.29 nM PMID[572884]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 57.81 nM PMID[572884]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 64.71 nM PMID[572884]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 63.53 nM PMID[572884]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 252.93 nM PMID[572884]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 42.17 nM PMID[572884]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 248.89 nM PMID[572884]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 49.43 nM PMID[572884]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 31.77 nM PMID[572884]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 65.46 nM PMID[572884]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 359.75 nM PMID[572884]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 58.75 nM PMID[572884]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 57.28 nM PMID[572884]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 54.2 nM PMID[572884]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 10.0 nM PMID[572884]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 52.12 nM PMID[572884]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 48.87 nM PMID[572884]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 61.24 nM PMID[572884]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 44.26 nM PMID[572884]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 53.58 nM PMID[572884]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 37.07 nM PMID[572884]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 290.4 nM PMID[572884]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 52.36 nM PMID[572884]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 55.59 nM PMID[572884]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 67.61 nM PMID[572884]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 223.87 nM PMID[572884]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 10.0 nM PMID[572884]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 493.17 nM PMID[572884]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 53.95 nM PMID[572884]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 51.52 nM PMID[572884]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 57.41 nM PMID[572884]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 63.83 nM PMID[572884]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 44.46 nM PMID[572884]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 59.84 nM PMID[572884]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 10.0 nM PMID[572884]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 45.29 nM PMID[572884]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 56.62 nM PMID[572884]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 62.23 nM PMID[572884]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 73.28 nM PMID[572884]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 40.36 nM PMID[572884]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 47.42 nM PMID[572884]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 48.19 nM PMID[572884]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 55.72 nM PMID[572884]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 50.0 nM PMID[572884]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 58.08 nM PMID[572884]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 50.82 nM PMID[572884]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 44.06 nM PMID[572884]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 56.49 nM PMID[572884]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 52.36 nM PMID[572884]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 35.89 nM PMID[572884]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 28.91 nM PMID[572884]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 270.4 nM PMID[572884]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 58.61 nM PMID[572884]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 61.94 nM PMID[572884]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 38.99 nM PMID[572884]
NPT2 Others Unspecified IC50 = 12.0 nM PMID[572883]
NPT2 Others Unspecified IC50 = 80.0 nM PMID[572883]
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens IC50 = 110.0 nM PMID[572883]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC233650 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9934 High Similarity NPC134858
0.9805 High Similarity NPC210140
0.9805 High Similarity NPC150879
0.9342 High Similarity NPC26601
0.9299 High Similarity NPC169743
0.9286 High Similarity NPC186063
0.9272 High Similarity NPC219162
0.9205 High Similarity NPC130941
0.9139 High Similarity NPC95075
0.9139 High Similarity NPC253883
0.9139 High Similarity NPC90844
0.8974 High Similarity NPC244112
0.8938 High Similarity NPC76116
0.8896 High Similarity NPC92541
0.8862 High Similarity NPC248642
0.8855 High Similarity NPC126284
0.8812 High Similarity NPC60186
0.881 High Similarity NPC156576
0.8773 High Similarity NPC164429
0.8773 High Similarity NPC160570
0.8766 High Similarity NPC144863
0.8758 High Similarity NPC185838
0.875 High Similarity NPC27410
0.875 High Similarity NPC166014
0.8734 High Similarity NPC76079
0.8712 High Similarity NPC298979
0.871 High Similarity NPC24233
0.871 High Similarity NPC476571
0.871 High Similarity NPC147390
0.871 High Similarity NPC428
0.871 High Similarity NPC246587
0.871 High Similarity NPC135538
0.8679 High Similarity NPC147091
0.8662 High Similarity NPC326316
0.8662 High Similarity NPC81733
0.8645 High Similarity NPC321505
0.8645 High Similarity NPC476151
0.8645 High Similarity NPC179825
0.8645 High Similarity NPC191376
0.8642 High Similarity NPC324144
0.8634 High Similarity NPC205167
0.8618 High Similarity NPC474915
0.8618 High Similarity NPC188163
0.8618 High Similarity NPC213206
0.8618 High Similarity NPC328750
0.8614 High Similarity NPC2314
0.8606 High Similarity NPC329911
0.8599 High Similarity NPC97221
0.8599 High Similarity NPC88249
0.8599 High Similarity NPC151895
0.8599 High Similarity NPC220858
0.8599 High Similarity NPC192768
0.8599 High Similarity NPC274026
0.8598 High Similarity NPC474931
0.8598 High Similarity NPC306555
0.8598 High Similarity NPC158376
0.8598 High Similarity NPC81218
0.8598 High Similarity NPC145832
0.8598 High Similarity NPC12053
0.8598 High Similarity NPC117188
0.8598 High Similarity NPC205421
0.8596 High Similarity NPC214116
0.8589 High Similarity NPC212794
0.8589 High Similarity NPC13504
0.8589 High Similarity NPC136508
0.8589 High Similarity NPC96603
0.8589 High Similarity NPC196447
0.8589 High Similarity NPC253043
0.8589 High Similarity NPC477563
0.8589 High Similarity NPC78222
0.8589 High Similarity NPC306843
0.8571 High Similarity NPC59028
0.8571 High Similarity NPC92191
0.8553 High Similarity NPC314682
0.8535 High Similarity NPC477565
0.8535 High Similarity NPC103379
0.8519 High Similarity NPC232924
0.8519 High Similarity NPC249274
0.8519 High Similarity NPC266753
0.8519 High Similarity NPC160298
0.8519 High Similarity NPC477559
0.8519 High Similarity NPC306902
0.8509 High Similarity NPC476572
0.8506 High Similarity NPC136860
0.8506 High Similarity NPC128019
0.8506 High Similarity NPC476567
0.85 High Similarity NPC99659
0.85 High Similarity NPC325871
0.85 High Similarity NPC127674
0.85 High Similarity NPC189266
0.85 High Similarity NPC172765
0.85 High Similarity NPC295691
0.85 High Similarity NPC39701
0.85 High Similarity NPC207757
0.85 High Similarity NPC193949
0.85 High Similarity NPC184026
0.85 High Similarity NPC204828
0.85 High Similarity NPC2413
0.85 High Similarity NPC469817
0.85 High Similarity NPC276588
0.85 High Similarity NPC5238
0.85 High Similarity NPC54379
0.85 High Similarity NPC249797
0.85 High Similarity NPC278799
0.85 High Similarity NPC110416
0.8471 Intermediate Similarity NPC475959
0.8462 Intermediate Similarity NPC114364
0.8462 Intermediate Similarity NPC320223
0.8462 Intermediate Similarity NPC148693
0.8462 Intermediate Similarity NPC118633
0.8462 Intermediate Similarity NPC294790
0.8457 Intermediate Similarity NPC111485
0.8457 Intermediate Similarity NPC477080
0.8452 Intermediate Similarity NPC229166
0.8452 Intermediate Similarity NPC128560
0.8452 Intermediate Similarity NPC199465
0.8443 Intermediate Similarity NPC477640
0.8443 Intermediate Similarity NPC470739
0.8443 Intermediate Similarity NPC225597
0.8434 Intermediate Similarity NPC58766
0.8434 Intermediate Similarity NPC266176
0.8434 Intermediate Similarity NPC290759
0.8434 Intermediate Similarity NPC158148
0.8434 Intermediate Similarity NPC475686
0.8434 Intermediate Similarity NPC82533
0.8424 Intermediate Similarity NPC476573
0.8424 Intermediate Similarity NPC24264
0.8424 Intermediate Similarity NPC35627
0.8424 Intermediate Similarity NPC81247
0.8424 Intermediate Similarity NPC476432
0.8421 Intermediate Similarity NPC476575
0.8418 Intermediate Similarity NPC207824
0.8418 Intermediate Similarity NPC60538
0.8415 Intermediate Similarity NPC1229
0.8408 Intermediate Similarity NPC476144
0.8408 Intermediate Similarity NPC106295
0.8408 Intermediate Similarity NPC210437
0.8408 Intermediate Similarity NPC16107
0.8408 Intermediate Similarity NPC51957
0.8405 Intermediate Similarity NPC97072
0.8405 Intermediate Similarity NPC215829
0.8383 Intermediate Similarity NPC474475
0.8375 Intermediate Similarity NPC133011
0.8375 Intermediate Similarity NPC82285
0.8373 Intermediate Similarity NPC247389
0.8364 Intermediate Similarity NPC276944
0.8364 Intermediate Similarity NPC167546
0.8364 Intermediate Similarity NPC238530
0.8364 Intermediate Similarity NPC225774
0.8364 Intermediate Similarity NPC16805
0.8364 Intermediate Similarity NPC302527
0.8364 Intermediate Similarity NPC232514
0.8354 Intermediate Similarity NPC7467
0.8344 Intermediate Similarity NPC221864
0.8333 Intermediate Similarity NPC126519
0.8333 Intermediate Similarity NPC239775
0.8333 Intermediate Similarity NPC170503
0.8333 Intermediate Similarity NPC203784
0.8313 Intermediate Similarity NPC219341
0.8313 Intermediate Similarity NPC250846
0.8313 Intermediate Similarity NPC268503
0.8313 Intermediate Similarity NPC277669
0.8313 Intermediate Similarity NPC240841
0.8313 Intermediate Similarity NPC317272
0.8313 Intermediate Similarity NPC76213
0.8313 Intermediate Similarity NPC42549
0.8313 Intermediate Similarity NPC256012
0.8295 Intermediate Similarity NPC117717
0.8294 Intermediate Similarity NPC241704
0.8293 Intermediate Similarity NPC205255
0.8293 Intermediate Similarity NPC119649
0.8293 Intermediate Similarity NPC235143
0.8293 Intermediate Similarity NPC230956
0.8293 Intermediate Similarity NPC271388
0.8284 Intermediate Similarity NPC477020
0.8284 Intermediate Similarity NPC192135
0.8284 Intermediate Similarity NPC66341
0.828 Intermediate Similarity NPC130926
0.8274 Intermediate Similarity NPC118274
0.8274 Intermediate Similarity NPC69712
0.8274 Intermediate Similarity NPC26240
0.8274 Intermediate Similarity NPC152212
0.8274 Intermediate Similarity NPC168753
0.8274 Intermediate Similarity NPC477562
0.8272 Intermediate Similarity NPC216459
0.8272 Intermediate Similarity NPC41178
0.8272 Intermediate Similarity NPC138487
0.8263 Intermediate Similarity NPC181653
0.8263 Intermediate Similarity NPC100566
0.8263 Intermediate Similarity NPC210918
0.8263 Intermediate Similarity NPC190332
0.8261 Intermediate Similarity NPC210148
0.8261 Intermediate Similarity NPC233029
0.8258 Intermediate Similarity NPC470925
0.8242 Intermediate Similarity NPC79402
0.8242 Intermediate Similarity NPC80759
0.8221 Intermediate Similarity NPC146288
0.8221 Intermediate Similarity NPC247639
0.8221 Intermediate Similarity NPC25084
0.8214 Intermediate Similarity NPC241055

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC233650 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8679 High Similarity NPD6818 Clinical (unspecified phase)
0.8642 High Similarity NPD7201 Clinical (unspecified phase)
0.8618 High Similarity NPD4664 Clinical (unspecified phase)
0.8571 High Similarity NPD5241 Discontinued
0.8408 Intermediate Similarity NPD4584 Approved
0.8293 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD7831 Phase 2
0.8293 Intermediate Similarity NPD7833 Phase 2
0.8232 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD4773 Phase 2
0.821 Intermediate Similarity NPD4772 Phase 2
0.8204 Intermediate Similarity NPD3051 Approved
0.8165 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD2969 Approved
0.8155 Intermediate Similarity NPD2970 Approved
0.8107 Intermediate Similarity NPD2489 Approved
0.8107 Intermediate Similarity NPD27 Approved
0.8 Intermediate Similarity NPD2421 Approved
0.8 Intermediate Similarity NPD2420 Approved
0.7988 Intermediate Similarity NPD6071 Discontinued
0.7975 Intermediate Similarity NPD4236 Phase 3
0.7975 Intermediate Similarity NPD4017 Approved
0.7975 Intermediate Similarity NPD4237 Approved
0.7966 Intermediate Similarity NPD7906 Approved
0.7963 Intermediate Similarity NPD6030 Approved
0.7963 Intermediate Similarity NPD6031 Approved
0.7952 Intermediate Similarity NPD2560 Approved
0.7952 Intermediate Similarity NPD2563 Approved
0.7939 Intermediate Similarity NPD7298 Approved
0.7937 Intermediate Similarity NPD3845 Phase 1
0.7917 Intermediate Similarity NPD7400 Phase 3
0.7911 Intermediate Similarity NPD7037 Approved
0.791 Intermediate Similarity NPD4663 Approved
0.7895 Intermediate Similarity NPD2898 Approved
0.7882 Intermediate Similarity NPD4010 Discontinued
0.7862 Intermediate Similarity NPD3060 Approved
0.7841 Intermediate Similarity NPD4578 Approved
0.7841 Intermediate Similarity NPD4577 Approved
0.7797 Intermediate Similarity NPD8053 Approved
0.7797 Intermediate Similarity NPD8054 Approved
0.7764 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD8156 Discontinued
0.775 Intermediate Similarity NPD5177 Phase 3
0.7744 Intermediate Similarity NPD3640 Phase 3
0.7744 Intermediate Similarity NPD3639 Approved
0.7744 Intermediate Similarity NPD3641 Approved
0.773 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD7802 Discontinued
0.7701 Intermediate Similarity NPD8252 Approved
0.7701 Intermediate Similarity NPD8099 Discontinued
0.7701 Intermediate Similarity NPD8251 Approved
0.7692 Intermediate Similarity NPD6788 Approved
0.7688 Intermediate Similarity NPD4481 Phase 3
0.7683 Intermediate Similarity NPD6090 Discontinued
0.7679 Intermediate Similarity NPD2978 Approved
0.7679 Intermediate Similarity NPD2977 Approved
0.7677 Intermediate Similarity NPD5718 Phase 2
0.767 Intermediate Similarity NPD6297 Approved
0.764 Intermediate Similarity NPD7311 Approved
0.764 Intermediate Similarity NPD7313 Approved
0.764 Intermediate Similarity NPD7312 Approved
0.764 Intermediate Similarity NPD7310 Approved
0.764 Intermediate Similarity NPD4162 Approved
0.7616 Intermediate Similarity NPD6107 Approved
0.7613 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD7309 Approved
0.7598 Intermediate Similarity NPD6853 Approved
0.7598 Intermediate Similarity NPD6851 Approved
0.758 Intermediate Similarity NPD3110 Approved
0.758 Intermediate Similarity NPD3109 Approved
0.7574 Intermediate Similarity NPD5773 Approved
0.7574 Intermediate Similarity NPD5772 Approved
0.7564 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6688 Approved
0.7529 Intermediate Similarity NPD6687 Approved
0.7516 Intermediate Similarity NPD4474 Approved
0.7516 Intermediate Similarity NPD4475 Approved
0.75 Intermediate Similarity NPD1753 Discontinued
0.75 Intermediate Similarity NPD5709 Phase 3
0.75 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD2488 Approved
0.7486 Intermediate Similarity NPD2490 Approved
0.7485 Intermediate Similarity NPD6331 Phase 2
0.7484 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD2973 Approved
0.7473 Intermediate Similarity NPD2975 Approved
0.7473 Intermediate Similarity NPD2974 Approved
0.7471 Intermediate Similarity NPD4166 Phase 2
0.7457 Intermediate Similarity NPD4666 Phase 3
0.7443 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD6895 Approved
0.7438 Intermediate Similarity NPD6896 Approved
0.7412 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD4123 Phase 3
0.7407 Intermediate Similarity NPD2494 Approved
0.7407 Intermediate Similarity NPD3452 Approved
0.7407 Intermediate Similarity NPD3450 Approved
0.7407 Intermediate Similarity NPD2493 Approved
0.7403 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6607 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD4580 Approved
0.7353 Intermediate Similarity NPD7438 Suspended
0.7349 Intermediate Similarity NPD3124 Discontinued
0.7348 Intermediate Similarity NPD2971 Approved
0.7348 Intermediate Similarity NPD2968 Approved
0.7345 Intermediate Similarity NPD5938 Phase 3
0.7342 Intermediate Similarity NPD7294 Phase 1
0.7337 Intermediate Similarity NPD4005 Discontinued
0.7333 Intermediate Similarity NPD5160 Discontinued
0.7326 Intermediate Similarity NPD5582 Discontinued
0.7326 Intermediate Similarity NPD5977 Approved
0.7326 Intermediate Similarity NPD5978 Approved
0.7321 Intermediate Similarity NPD5976 Discontinued
0.7308 Intermediate Similarity NPD6584 Phase 3
0.7305 Intermediate Similarity NPD7019 Approved
0.7305 Intermediate Similarity NPD7020 Approved
0.7301 Intermediate Similarity NPD7030 Discontinued
0.7297 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD2674 Phase 3
0.7293 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD4582 Approved
0.7292 Intermediate Similarity NPD4583 Approved
0.7283 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5155 Approved
0.7278 Intermediate Similarity NPD5156 Approved
0.7278 Intermediate Similarity NPD4210 Discontinued
0.7273 Intermediate Similarity NPD6747 Phase 1
0.7273 Intermediate Similarity NPD6748 Discontinued
0.7273 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD42 Phase 2
0.7263 Intermediate Similarity NPD6042 Phase 2
0.7263 Intermediate Similarity NPD5312 Approved
0.7263 Intermediate Similarity NPD5313 Approved
0.7262 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD7281 Phase 3
0.7253 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD7280 Phase 3
0.725 Intermediate Similarity NPD2238 Phase 2
0.7249 Intermediate Similarity NPD4420 Approved
0.7246 Intermediate Similarity NPD7598 Phase 2
0.7244 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD4103 Phase 2
0.724 Intermediate Similarity NPD4002 Approved
0.724 Intermediate Similarity NPD4004 Approved
0.7239 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7039 Approved
0.7238 Intermediate Similarity NPD7038 Approved
0.7229 Intermediate Similarity NPD3692 Discontinued
0.7226 Intermediate Similarity NPD4659 Approved
0.7226 Intermediate Similarity NPD1669 Approved
0.7225 Intermediate Similarity NPD6063 Approved
0.7222 Intermediate Similarity NPD7479 Phase 2
0.7222 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7262 Phase 1
0.7219 Intermediate Similarity NPD4727 Phase 1
0.7219 Intermediate Similarity NPD1914 Approved
0.7215 Intermediate Similarity NPD3594 Approved
0.7215 Intermediate Similarity NPD2605 Approved
0.7215 Intermediate Similarity NPD3595 Approved
0.7215 Intermediate Similarity NPD2606 Approved
0.7209 Intermediate Similarity NPD4227 Discontinued
0.7204 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD3645 Discontinued
0.7202 Intermediate Similarity NPD2874 Phase 2
0.7193 Intermediate Similarity NPD4675 Approved
0.7193 Intermediate Similarity NPD4678 Approved
0.7189 Intermediate Similarity NPD7291 Discontinued
0.7182 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD2156 Approved
0.7178 Intermediate Similarity NPD2154 Approved
0.7178 Intermediate Similarity NPD2155 Approved
0.7167 Intermediate Similarity NPD4873 Discontinued
0.7159 Intermediate Similarity NPD2904 Discontinued
0.7158 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD3635 Approved
0.7152 Intermediate Similarity NPD3636 Approved
0.7152 Intermediate Similarity NPD3637 Approved
0.7151 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD7110 Phase 1
0.7143 Intermediate Similarity NPD3620 Phase 2
0.7143 Intermediate Similarity NPD6997 Phase 2
0.7143 Intermediate Similarity NPD4055 Discovery
0.7143 Intermediate Similarity NPD5604 Discontinued
0.7143 Intermediate Similarity NPD7213 Phase 3
0.7143 Intermediate Similarity NPD7212 Phase 2
0.7143 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD4083 Discontinued
0.7134 Intermediate Similarity NPD2161 Phase 2
0.7125 Intermediate Similarity NPD3144 Approved
0.7125 Intermediate Similarity NPD3145 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data