Structure

Physi-Chem Properties

Molecular Weight:  271.12
Volume:  269.332
LogP:  1.285
LogD:  1.057
LogS:  -2.624
# Rotatable Bonds:  0
TPSA:  41.93
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.727
Synthetic Accessibility Score:  4.846
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.756
MDCK Permeability:  2.1714653485105373e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.843
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.019
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.991
Plasma Protein Binding (PPB):  43.71992492675781%
Volume Distribution (VD):  2.889
Pgp-substrate:  52.57981491088867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.773
CYP1A2-substrate:  0.5
CYP2C19-inhibitor:  0.593
CYP2C19-substrate:  0.814
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.375
CYP2D6-inhibitor:  0.97
CYP2D6-substrate:  0.876
CYP3A4-inhibitor:  0.869
CYP3A4-substrate:  0.555

ADMET: Excretion

Clearance (CL):  11.704
Half-life (T1/2):  0.633

ADMET: Toxicity

hERG Blockers:  0.183
Human Hepatotoxicity (H-HT):  0.183
Drug-inuced Liver Injury (DILI):  0.039
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.444
Maximum Recommended Daily Dose:  0.963
Skin Sensitization:  0.125
Carcinogencity:  0.908
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.901

Download Data

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

  Natural Product: NPC215829

Natural Product ID:  NPC215829
Common Name*:   RPAORVSEYNOMBR-LYRGGWFBSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  RPAORVSEYNOMBR-LYRGGWFBSA-N
Standard InCHI:  InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15-,16+/m1/s1
SMILES:  O[C@@H]1C=C[C@]23[C@@H](C1)N(CC2)Cc1c3cc2OCOc2c1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1971343
PubChem CID:   398938
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001775] Amaryllidaceae alkaloids
        • [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae alkaloids

*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
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26299 Reticularia lycoperdon Species Reticulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19610 Stachys aegyptiaca Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17432 Ligularia przewalskii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO389 Actaea heracleifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13181 Ferula persica Species Apiaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 69342.58 nM PMID[570231]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 32658.78 nM PMID[570231]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 35237.09 nM PMID[570231]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 48194.78 nM PMID[570231]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 65614.53 nM PMID[570231]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 24660.39 nM PMID[570231]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 61094.2 nM PMID[570231]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 92044.96 nM PMID[570231]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 41209.75 nM PMID[570231]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 54075.43 nM PMID[570231]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 58210.32 nM PMID[570231]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 43052.66 nM PMID[570231]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 67764.15 nM PMID[570231]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 49773.71 nM PMID[570231]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 48977.88 nM PMID[570231]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 52480.75 nM PMID[570231]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 82413.81 nM PMID[570231]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 50699.07 nM PMID[570231]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 60813.5 nM PMID[570231]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 34040.82 nM PMID[570231]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 48417.24 nM PMID[570231]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 31260.79 nM PMID[570231]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 46558.61 nM PMID[570231]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 20511.62 nM PMID[570231]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 42756.29 nM PMID[570231]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 87096.36 nM PMID[570231]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 45185.59 nM PMID[570231]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 52119.47 nM PMID[570231]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 39084.09 nM PMID[570231]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 42657.95 nM PMID[570231]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 26791.68 nM PMID[570231]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 57016.43 nM PMID[570231]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 39994.47 nM PMID[570231]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 44258.84 nM PMID[570231]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 56754.46 nM PMID[570231]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 92044.96 nM PMID[570231]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 48865.24 nM PMID[570231]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 51522.86 nM PMID[570231]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[570231]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 20844.91 nM PMID[570231]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 44771.33 nM PMID[570231]

☑ 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 NPC215829 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
1.0 High Similarity NPC97072
0.9613 High Similarity NPC58766
0.9613 High Similarity NPC475686
0.96 High Similarity NPC78733
0.9551 High Similarity NPC474475
0.949 High Similarity NPC225597
0.949 High Similarity NPC477640
0.949 High Similarity NPC470739
0.9487 High Similarity NPC290759
0.9487 High Similarity NPC82533
0.9487 High Similarity NPC158148
0.9487 High Similarity NPC266176
0.9355 High Similarity NPC320104
0.9299 High Similarity NPC181653
0.9299 High Similarity NPC190332
0.9299 High Similarity NPC100566
0.9281 High Similarity NPC147091
0.9193 High Similarity NPC474470
0.9182 High Similarity NPC311991
0.9085 High Similarity NPC148898
0.908 High Similarity NPC244554
0.9051 High Similarity NPC247972
0.8961 High Similarity NPC223124
0.8957 High Similarity NPC237044
0.8954 High Similarity NPC274026
0.8944 High Similarity NPC75958
0.8938 High Similarity NPC252960
0.8902 High Similarity NPC474325
0.8902 High Similarity NPC15919
0.8896 High Similarity NPC304675
0.8875 High Similarity NPC476002
0.8868 High Similarity NPC218614
0.8848 High Similarity NPC474745
0.8831 High Similarity NPC223125
0.8824 High Similarity NPC475959
0.879 High Similarity NPC234392
0.879 High Similarity NPC31311
0.8742 High Similarity NPC205167
0.8742 High Similarity NPC249274
0.872 High Similarity NPC2314
0.8718 High Similarity NPC210148
0.8718 High Similarity NPC82285
0.8718 High Similarity NPC233029
0.8718 High Similarity NPC133011
0.8704 High Similarity NPC57812
0.8704 High Similarity NPC474324
0.8696 High Similarity NPC276944
0.8696 High Similarity NPC238530
0.8696 High Similarity NPC232514
0.869 High Similarity NPC475981
0.869 High Similarity NPC474746
0.8679 High Similarity NPC111485
0.8675 High Similarity NPC148693
0.8675 High Similarity NPC118633
0.8675 High Similarity NPC294790
0.8667 High Similarity NPC187678
0.8659 High Similarity NPC65403
0.865 High Similarity NPC475845
0.8639 High Similarity NPC9867
0.8627 High Similarity NPC185838
0.8627 High Similarity NPC130926
0.8625 High Similarity NPC4304
0.8608 High Similarity NPC41178
0.8608 High Similarity NPC216459
0.8608 High Similarity NPC138487
0.8598 High Similarity NPC474708
0.8588 High Similarity NPC230098
0.858 High Similarity NPC231198
0.8562 High Similarity NPC59028
0.8562 High Similarity NPC92191
0.8562 High Similarity NPC477080
0.8553 High Similarity NPC146288
0.8521 High Similarity NPC102760
0.8516 High Similarity NPC476151
0.8516 High Similarity NPC191376
0.8516 High Similarity NPC321505
0.8516 High Similarity NPC179825
0.8509 High Similarity NPC165797
0.8476 Intermediate Similarity NPC298979
0.8467 Intermediate Similarity NPC7018
0.8462 Intermediate Similarity NPC147390
0.8462 Intermediate Similarity NPC246587
0.8462 Intermediate Similarity NPC135538
0.8462 Intermediate Similarity NPC428
0.8462 Intermediate Similarity NPC476571
0.8462 Intermediate Similarity NPC24233
0.8443 Intermediate Similarity NPC49353
0.8421 Intermediate Similarity NPC314682
0.8412 Intermediate Similarity NPC275132
0.8408 Intermediate Similarity NPC103379
0.8408 Intermediate Similarity NPC477565
0.8405 Intermediate Similarity NPC59567
0.8405 Intermediate Similarity NPC233650
0.8402 Intermediate Similarity NPC126284
0.8375 Intermediate Similarity NPC76079
0.8366 Intermediate Similarity NPC213206
0.8366 Intermediate Similarity NPC188163
0.8366 Intermediate Similarity NPC328750
0.8366 Intermediate Similarity NPC474915
0.8354 Intermediate Similarity NPC134858
0.8304 Intermediate Similarity NPC248642
0.8291 Intermediate Similarity NPC207824
0.8291 Intermediate Similarity NPC60538
0.8284 Intermediate Similarity NPC283999
0.8282 Intermediate Similarity NPC266753
0.8282 Intermediate Similarity NPC306902
0.8282 Intermediate Similarity NPC477559
0.8282 Intermediate Similarity NPC160298
0.8282 Intermediate Similarity NPC232924
0.8272 Intermediate Similarity NPC475326
0.8272 Intermediate Similarity NPC78359
0.8272 Intermediate Similarity NPC65490
0.8272 Intermediate Similarity NPC40389
0.8272 Intermediate Similarity NPC315707
0.8272 Intermediate Similarity NPC148014
0.8261 Intermediate Similarity NPC469817
0.8261 Intermediate Similarity NPC276588
0.8261 Intermediate Similarity NPC110416
0.8261 Intermediate Similarity NPC295691
0.8261 Intermediate Similarity NPC5238
0.8261 Intermediate Similarity NPC93593
0.8261 Intermediate Similarity NPC127674
0.8261 Intermediate Similarity NPC278799
0.8261 Intermediate Similarity NPC39701
0.8261 Intermediate Similarity NPC172765
0.8261 Intermediate Similarity NPC54379
0.8261 Intermediate Similarity NPC189266
0.8261 Intermediate Similarity NPC193949
0.8261 Intermediate Similarity NPC2413
0.8261 Intermediate Similarity NPC204828
0.8261 Intermediate Similarity NPC207757
0.8261 Intermediate Similarity NPC249797
0.8261 Intermediate Similarity NPC184026
0.8256 Intermediate Similarity NPC156576
0.8253 Intermediate Similarity NPC150879
0.8253 Intermediate Similarity NPC210140
0.8239 Intermediate Similarity NPC220858
0.8239 Intermediate Similarity NPC192768
0.8239 Intermediate Similarity NPC97221
0.8239 Intermediate Similarity NPC151895
0.8239 Intermediate Similarity NPC88249
0.8221 Intermediate Similarity NPC106786
0.8214 Intermediate Similarity NPC476331
0.8193 Intermediate Similarity NPC124657
0.8187 Intermediate Similarity NPC76213
0.8187 Intermediate Similarity NPC277669
0.8171 Intermediate Similarity NPC18402
0.8165 Intermediate Similarity NPC51957
0.8165 Intermediate Similarity NPC106295
0.8165 Intermediate Similarity NPC16107
0.8165 Intermediate Similarity NPC476144
0.8165 Intermediate Similarity NPC210437
0.8155 Intermediate Similarity NPC152212
0.8144 Intermediate Similarity NPC210918
0.8141 Intermediate Similarity NPC476567
0.8141 Intermediate Similarity NPC128019
0.8141 Intermediate Similarity NPC136860
0.8137 Intermediate Similarity NPC26601
0.8133 Intermediate Similarity NPC225774
0.8129 Intermediate Similarity NPC114364
0.8129 Intermediate Similarity NPC320223
0.8118 Intermediate Similarity NPC128560
0.8118 Intermediate Similarity NPC199465
0.8118 Intermediate Similarity NPC229166
0.8113 Intermediate Similarity NPC7467
0.8105 Intermediate Similarity NPC131204
0.8105 Intermediate Similarity NPC301050
0.8098 Intermediate Similarity NPC323443
0.8098 Intermediate Similarity NPC180756
0.8095 Intermediate Similarity NPC470324
0.8092 Intermediate Similarity NPC476575
0.8092 Intermediate Similarity NPC233718
0.8086 Intermediate Similarity NPC477564
0.8086 Intermediate Similarity NPC2295
0.8084 Intermediate Similarity NPC219341
0.8084 Intermediate Similarity NPC476432
0.8084 Intermediate Similarity NPC24264
0.8081 Intermediate Similarity NPC99179
0.8067 Intermediate Similarity NPC160193
0.8063 Intermediate Similarity NPC219162
0.8057 Intermediate Similarity NPC214116
0.8049 Intermediate Similarity NPC129603
0.8036 Intermediate Similarity NPC247389
0.8036 Intermediate Similarity NPC298186
0.8036 Intermediate Similarity NPC301189
0.8025 Intermediate Similarity NPC37272
0.8024 Intermediate Similarity NPC167546
0.8024 Intermediate Similarity NPC180306
0.8024 Intermediate Similarity NPC76116
0.8024 Intermediate Similarity NPC302527
0.8024 Intermediate Similarity NPC16805
0.8024 Intermediate Similarity NPC168409
0.8012 Intermediate Similarity NPC477558
0.8 Intermediate Similarity NPC118804
0.8 Intermediate Similarity NPC59907
0.8 Intermediate Similarity NPC37144
0.7988 Intermediate Similarity NPC241055
0.7988 Intermediate Similarity NPC186063
0.7987 Intermediate Similarity NPC416184
0.7976 Intermediate Similarity NPC304659

  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 NPC215829 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
0.8428 Intermediate Similarity NPD4773 Phase 2
0.8428 Intermediate Similarity NPD4772 Phase 2
0.8366 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD6071 Discontinued
0.8272 Intermediate Similarity NPD2560 Approved
0.8272 Intermediate Similarity NPD2563 Approved
0.8205 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8165 Intermediate Similarity NPD4584 Approved
0.8144 Intermediate Similarity NPD2969 Approved
0.8144 Intermediate Similarity NPD2970 Approved
0.8095 Intermediate Similarity NPD27 Approved
0.8095 Intermediate Similarity NPD2898 Approved
0.8095 Intermediate Similarity NPD2489 Approved
0.8089 Intermediate Similarity NPD5241 Discontinued
0.8038 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD3051 Approved
0.7879 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD4017 Approved
0.7844 Intermediate Similarity NPD7831 Phase 2
0.7844 Intermediate Similarity NPD7833 Phase 2
0.7844 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD3641 Approved
0.784 Intermediate Similarity NPD3639 Approved
0.784 Intermediate Similarity NPD3640 Phase 3
0.7829 Intermediate Similarity NPD7281 Phase 3
0.7829 Intermediate Similarity NPD7280 Phase 3
0.7771 Intermediate Similarity NPD2978 Approved
0.7771 Intermediate Similarity NPD2977 Approved
0.7751 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD6107 Approved
0.7674 Intermediate Similarity NPD4481 Phase 3
0.7661 Intermediate Similarity NPD4010 Discontinued
0.7625 Intermediate Similarity NPD4236 Phase 3
0.7625 Intermediate Similarity NPD4237 Approved
0.7622 Intermediate Similarity NPD6030 Approved
0.7622 Intermediate Similarity NPD6031 Approved
0.7613 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD7298 Approved
0.7596 Intermediate Similarity NPD5582 Discontinued
0.756 Intermediate Similarity NPD5772 Approved
0.756 Intermediate Similarity NPD5773 Approved
0.7558 Intermediate Similarity NPD4166 Phase 2
0.7529 Intermediate Similarity NPD5604 Discontinued
0.7528 Intermediate Similarity NPD4578 Approved
0.7528 Intermediate Similarity NPD7313 Approved
0.7528 Intermediate Similarity NPD4577 Approved
0.7528 Intermediate Similarity NPD7311 Approved
0.7528 Intermediate Similarity NPD7310 Approved
0.7528 Intermediate Similarity NPD7312 Approved
0.7516 Intermediate Similarity NPD5177 Phase 3
0.7514 Intermediate Similarity NPD4420 Approved
0.75 Intermediate Similarity NPD4663 Approved
0.7486 Intermediate Similarity NPD7309 Approved
0.7468 Intermediate Similarity NPD2492 Phase 1
0.7459 Intermediate Similarity NPD7906 Approved
0.7447 Intermediate Similarity NPD5005 Approved
0.7447 Intermediate Similarity NPD5006 Approved
0.7443 Intermediate Similarity NPD5312 Approved
0.7443 Intermediate Similarity NPD5313 Approved
0.7436 Intermediate Similarity NPD5718 Phase 2
0.7389 Intermediate Similarity NPD8053 Approved
0.7389 Intermediate Similarity NPD8054 Approved
0.7375 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6297 Approved
0.7345 Intermediate Similarity NPD8156 Discontinued
0.7337 Intermediate Similarity NPD7296 Approved
0.7333 Intermediate Similarity NPD3124 Discontinued
0.7333 Intermediate Similarity NPD1357 Approved
0.7312 Intermediate Similarity NPD6895 Approved
0.7312 Intermediate Similarity NPD6896 Approved
0.7308 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4727 Phase 1
0.7301 Intermediate Similarity NPD3060 Approved
0.7294 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD6851 Approved
0.7293 Intermediate Similarity NPD6853 Approved
0.7288 Intermediate Similarity NPD8099 Discontinued
0.7288 Intermediate Similarity NPD8251 Approved
0.7288 Intermediate Similarity NPD8252 Approved
0.7283 Intermediate Similarity NPD2488 Approved
0.7283 Intermediate Similarity NPD2490 Approved
0.7283 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2674 Phase 3
0.7273 Intermediate Similarity NPD3845 Phase 1
0.7268 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6788 Approved
0.7267 Intermediate Similarity NPD1753 Discontinued
0.7262 Intermediate Similarity NPD4210 Discontinued
0.7233 Intermediate Similarity NPD3110 Approved
0.7233 Intermediate Similarity NPD3109 Approved
0.7233 Intermediate Similarity NPD2238 Phase 2
0.7232 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD2421 Approved
0.7229 Intermediate Similarity NPD2420 Approved
0.7222 Intermediate Similarity NPD2161 Phase 2
0.7195 Intermediate Similarity NPD4162 Approved
0.7186 Intermediate Similarity NPD7019 Approved
0.7186 Intermediate Similarity NPD7020 Approved
0.7175 Intermediate Similarity NPD6365 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2971 Approved
0.7143 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2968 Approved
0.7127 Intermediate Similarity NPD7149 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6687 Approved
0.7119 Intermediate Similarity NPD6688 Approved
0.7117 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD5978 Approved
0.711 Intermediate Similarity NPD5977 Approved
0.7108 Intermediate Similarity NPD3692 Discontinued
0.7107 Intermediate Similarity NPD3144 Approved
0.7107 Intermediate Similarity NPD3145 Approved
0.7104 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7802 Discontinued
0.7083 Intermediate Similarity NPD1424 Approved
0.7078 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4475 Approved
0.7063 Intermediate Similarity NPD4474 Approved
0.7062 Intermediate Similarity NPD7607 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2667 Approved
0.7059 Intermediate Similarity NPD2668 Approved
0.7048 Intermediate Similarity NPD6331 Phase 2
0.7041 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD52 Approved
0.7041 Intermediate Similarity NPD7526 Approved
0.7037 Intermediate Similarity NPD817 Approved
0.7037 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD823 Approved
0.7032 Intermediate Similarity NPD2230 Approved
0.7032 Intermediate Similarity NPD2233 Approved
0.7032 Intermediate Similarity NPD2232 Approved
0.7031 Intermediate Similarity NPD3452 Approved
0.7031 Intermediate Similarity NPD3450 Approved
0.703 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7037 Approved
0.7025 Intermediate Similarity NPD3636 Approved
0.7025 Intermediate Similarity NPD3637 Approved
0.7025 Intermediate Similarity NPD3635 Approved
0.7018 Intermediate Similarity NPD4005 Discontinued
0.7018 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD3885 Approved
0.7006 Intermediate Similarity NPD3983 Phase 3
0.7006 Intermediate Similarity NPD3984 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5160 Discontinued
0.7006 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2973 Approved
0.7 Intermediate Similarity NPD2974 Approved
0.7 Intermediate Similarity NPD2122 Discontinued
0.7 Intermediate Similarity NPD2975 Approved
0.6995 Remote Similarity NPD3448 Approved
0.6995 Remote Similarity NPD3057 Approved
0.6989 Remote Similarity NPD4796 Discontinued
0.6982 Remote Similarity NPD2874 Phase 2
0.6981 Remote Similarity NPD3594 Approved
0.6981 Remote Similarity NPD3595 Approved
0.6971 Remote Similarity NPD1742 Approved
0.6971 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6971 Remote Similarity NPD1743 Approved
0.6971 Remote Similarity NPD19 Approved
0.697 Remote Similarity NPD3656 Approved
0.697 Remote Similarity NPD1375 Discontinued
0.6964 Remote Similarity NPD7124 Phase 2
0.6959 Remote Similarity NPD3686 Approved
0.6959 Remote Similarity NPD3687 Approved
0.6952 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6951 Remote Similarity NPD4108 Discontinued
0.6949 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6949 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6946 Remote Similarity NPD6748 Discontinued
0.6946 Remote Similarity NPD5754 Discontinued
0.6943 Remote Similarity NPD2493 Approved
0.6943 Remote Similarity NPD2494 Approved
0.6928 Remote Similarity NPD7153 Discontinued
0.6923 Remote Similarity NPD4040 Phase 1
0.6914 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6914 Remote Similarity NPD3620 Phase 2
0.6907 Remote Similarity NPD2491 Approved
0.6907 Remote Similarity NPD2972 Approved
0.6907 Remote Similarity NPD3533 Approved
0.6904 Remote Similarity NPD4859 Phase 1
0.6899 Remote Similarity NPD4103 Phase 2
0.6899 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6898 Remote Similarity NPD3349 Phase 2
0.6897 Remote Similarity NPD3384 Approved
0.6897 Remote Similarity NPD3383 Approved
0.6897 Remote Similarity NPD3382 Approved
0.6897 Remote Similarity NPD5720 Discontinued
0.6893 Remote Similarity NPD7400 Phase 3
0.6891 Remote Similarity NPD4580 Approved
0.6882 Remote Similarity NPD4739 Approved
0.6882 Remote Similarity NPD4123 Phase 3
0.6879 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6878 Remote Similarity NPD6997 Phase 2
0.6875 Remote Similarity NPD2606 Approved
0.6875 Remote Similarity NPD2605 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