Structure

Physi-Chem Properties

Molecular Weight:  442.38
Volume:  499.598
LogP:  6.837
LogD:  5.192
LogS:  -5.261
# Rotatable Bonds:  0
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.391
Synthetic Accessibility Score:  4.723
Fsp3:  0.933
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.008
MDCK Permeability:  1.0937787010334432e-05
Pgp-inhibitor:  0.5
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.959
30% Bioavailability (F30%):  0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.466
Plasma Protein Binding (PPB):  95.30135345458984%
Volume Distribution (VD):  1.191
Pgp-substrate:  3.735316276550293%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.176
CYP2C19-inhibitor:  0.061
CYP2C19-substrate:  0.926
CYP2C9-inhibitor:  0.202
CYP2C9-substrate:  0.251
CYP2D6-inhibitor:  0.024
CYP2D6-substrate:  0.178
CYP3A4-inhibitor:  0.688
CYP3A4-substrate:  0.378

ADMET: Excretion

Clearance (CL):  8.984
Half-life (T1/2):  0.067

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.33
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.946
Maximum Recommended Daily Dose:  0.983
Skin Sensitization:  0.331
Carcinogencity:  0.074
Eye Corrosion:  0.238
Eye Irritation:  0.067
Respiratory Toxicity:  0.987

Download Data

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

  Natural Product: NPC34177

Natural Product ID:  NPC34177
Common Name*:   (3S,4Ar,6Ar,6Bs,8S,8As,12As,14Ar,14Br)-4,4,6A,6B,8A,11,11,14B-Octamethyl-1,2,3,4A,5,6,7,8,9,10,12,12A,14,14A-Tetradecahydropicene-3,8-Diol
IUPAC Name:   (3S,4aR,6aR,6bS,8S,8aS,12aS,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,8-diol
Synonyms:  
Standard InCHIKey:  VLRYIIPJIVGFIV-QQSFYHFXSA-N
Standard InCHI:  InChI=1S/C30H50O2/c1-25(2)15-16-27(5)20(17-25)19-9-10-22-28(6)13-12-23(31)26(3,4)21(28)11-14-29(22,7)30(19,8)18-24(27)32/h9,20-24,31-32H,10-18H2,1-8H3/t20-,21-,22+,23-,24-,27-,28-,29+,30+/m0/s1
SMILES:  CC1(C)CC[C@@]2(C)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@@H]2O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1977415
PubChem CID:   397934
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO11992 Cystoseira usneoides Species Sargassaceae Eukaryota n.a. n.a. n.a. PMID[23458950]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. inflorescence n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11992 Cystoseira usneoides Species Sargassaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 56885.29 nM PMID[515194]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 41399.97 nM PMID[515194]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 29444.22 nM PMID[515194]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 20417.38 nM PMID[515194]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 16180.8 nM PMID[515194]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 40644.33 nM PMID[515194]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 35318.32 nM PMID[515194]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 29376.5 nM PMID[515194]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 34276.78 nM PMID[515194]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 65162.84 nM PMID[515194]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 36982.82 nM PMID[515194]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 28707.81 nM PMID[515194]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 39994.47 nM PMID[515194]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 20276.83 nM PMID[515194]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 97274.72 nM PMID[515194]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 61517.69 nM PMID[515194]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 16788.04 nM PMID[515194]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 27861.21 nM PMID[515194]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 25703.96 nM PMID[515194]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 41399.97 nM PMID[515194]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 93110.79 nM PMID[515194]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 44258.84 nM PMID[515194]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 97274.72 nM PMID[515194]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 16405.9 nM PMID[515194]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 93110.79 nM PMID[515194]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 26363.31 nM PMID[515194]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 31695.67 nM PMID[515194]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 41495.4 nM PMID[515194]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 81096.11 nM PMID[515194]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 46344.69 nM PMID[515194]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 38815.04 nM PMID[515194]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 37931.5 nM PMID[515194]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 28973.44 nM PMID[515194]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 9794.9 nM PMID[515194]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 14927.94 nM PMID[515194]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 41209.75 nM PMID[515194]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 58748.94 nM PMID[515194]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 34514.37 nM PMID[515194]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 29444.22 nM PMID[515194]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 35892.19 nM PMID[515194]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 24378.11 nM PMID[515194]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 49545.02 nM PMID[515194]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 33342.64 nM PMID[515194]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 34994.52 nM PMID[515194]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 39174.19 nM PMID[515194]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[515194]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 48640.72 nM PMID[515194]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 7244.36 nM PMID[515194]

☑ 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 NPC34177 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 NPC157996
1.0 High Similarity NPC40394
1.0 High Similarity NPC101475
0.9861 High Similarity NPC22955
0.9861 High Similarity NPC196753
0.9861 High Similarity NPC470396
0.9861 High Similarity NPC158662
0.9861 High Similarity NPC253807
0.9861 High Similarity NPC230295
0.9861 High Similarity NPC98386
0.9861 High Similarity NPC99168
0.9861 High Similarity NPC300499
0.9861 High Similarity NPC474989
0.9859 High Similarity NPC30590
0.9859 High Similarity NPC122418
0.9859 High Similarity NPC120098
0.9859 High Similarity NPC290598
0.9859 High Similarity NPC265328
0.9859 High Similarity NPC27765
0.9726 High Similarity NPC53744
0.9726 High Similarity NPC291379
0.9718 High Similarity NPC34700
0.9718 High Similarity NPC138374
0.9595 High Similarity NPC295131
0.9583 High Similarity NPC106364
0.9577 High Similarity NPC100334
0.9467 High Similarity NPC242350
0.9452 High Similarity NPC472805
0.9452 High Similarity NPC90979
0.9342 High Similarity NPC47763
0.9342 High Similarity NPC304285
0.9324 High Similarity NPC72507
0.9221 High Similarity NPC253402
0.9221 High Similarity NPC159168
0.9211 High Similarity NPC116202
0.9167 High Similarity NPC182717
0.9167 High Similarity NPC211009
0.9103 High Similarity NPC238992
0.9041 High Similarity NPC91858
0.9041 High Similarity NPC243342
0.9041 High Similarity NPC477138
0.9028 High Similarity NPC167706
0.9028 High Similarity NPC301226
0.8987 High Similarity NPC133954
0.8987 High Similarity NPC191965
0.8974 High Similarity NPC237795
0.8974 High Similarity NPC82538
0.8933 High Similarity NPC470711
0.8933 High Similarity NPC471798
0.8933 High Similarity NPC470758
0.8919 High Similarity NPC66566
0.8919 High Similarity NPC477923
0.8919 High Similarity NPC144075
0.8919 High Similarity NPC291503
0.8904 High Similarity NPC471799
0.8875 High Similarity NPC235341
0.8875 High Similarity NPC213412
0.8875 High Similarity NPC84121
0.8875 High Similarity NPC95594
0.8875 High Similarity NPC137306
0.8875 High Similarity NPC237344
0.8875 High Similarity NPC74363
0.8875 High Similarity NPC477579
0.8875 High Similarity NPC475862
0.8846 High Similarity NPC248886
0.8816 High Similarity NPC167037
0.8816 High Similarity NPC285761
0.8816 High Similarity NPC6978
0.8816 High Similarity NPC138621
0.8816 High Similarity NPC244385
0.88 High Similarity NPC237460
0.88 High Similarity NPC189883
0.88 High Similarity NPC106432
0.88 High Similarity NPC470749
0.8784 High Similarity NPC471797
0.8767 High Similarity NPC110799
0.8767 High Similarity NPC242001
0.8765 High Similarity NPC142415
0.8765 High Similarity NPC102683
0.8765 High Similarity NPC242468
0.8765 High Similarity NPC307426
0.8765 High Similarity NPC293564
0.8765 High Similarity NPC68160
0.8765 High Similarity NPC88716
0.8765 High Similarity NPC171203
0.8765 High Similarity NPC18064
0.8765 High Similarity NPC73064
0.8765 High Similarity NPC98442
0.8765 High Similarity NPC51700
0.8765 High Similarity NPC130577
0.8701 High Similarity NPC472463
0.8701 High Similarity NPC273410
0.8701 High Similarity NPC80530
0.8701 High Similarity NPC1319
0.8684 High Similarity NPC477924
0.8684 High Similarity NPC91594
0.8684 High Similarity NPC214570
0.8684 High Similarity NPC130136
0.8667 High Similarity NPC141071
0.8667 High Similarity NPC240235
0.8667 High Similarity NPC104387
0.8667 High Similarity NPC178383
0.8667 High Similarity NPC231256
0.8667 High Similarity NPC212879
0.8667 High Similarity NPC257347
0.8667 High Similarity NPC471723
0.8659 High Similarity NPC181225
0.8659 High Similarity NPC17733
0.8659 High Similarity NPC474512
0.8659 High Similarity NPC52169
0.8659 High Similarity NPC473242
0.8659 High Similarity NPC470629
0.8659 High Similarity NPC246708
0.8659 High Similarity NPC290690
0.8659 High Similarity NPC182797
0.8659 High Similarity NPC40552
0.8642 High Similarity NPC72638
0.863 High Similarity NPC92801
0.863 High Similarity NPC145498
0.8625 High Similarity NPC180834
0.8625 High Similarity NPC209802
0.8611 High Similarity NPC94192
0.8611 High Similarity NPC208999
0.859 High Similarity NPC102253
0.859 High Similarity NPC13554
0.859 High Similarity NPC322313
0.859 High Similarity NPC236112
0.859 High Similarity NPC236237
0.8571 High Similarity NPC85346
0.8571 High Similarity NPC312328
0.8571 High Similarity NPC302041
0.8571 High Similarity NPC11908
0.8571 High Similarity NPC275910
0.8571 High Similarity NPC65897
0.8554 High Similarity NPC143232
0.8554 High Similarity NPC121798
0.8554 High Similarity NPC263393
0.8554 High Similarity NPC187785
0.8554 High Similarity NPC474972
0.8554 High Similarity NPC274330
0.8554 High Similarity NPC470588
0.8554 High Similarity NPC130520
0.8554 High Similarity NPC64872
0.8554 High Similarity NPC290972
0.8554 High Similarity NPC234346
0.8554 High Similarity NPC293048
0.8554 High Similarity NPC161751
0.8554 High Similarity NPC127689
0.8554 High Similarity NPC198664
0.8554 High Similarity NPC95246
0.8554 High Similarity NPC259875
0.8554 High Similarity NPC25906
0.8554 High Similarity NPC61543
0.8554 High Similarity NPC270768
0.8554 High Similarity NPC225585
0.8554 High Similarity NPC59263
0.8554 High Similarity NPC69627
0.8553 High Similarity NPC278091
0.8553 High Similarity NPC134330
0.8553 High Similarity NPC78067
0.8553 High Similarity NPC202642
0.8553 High Similarity NPC240604
0.8553 High Similarity NPC265588
0.8553 High Similarity NPC129165
0.8553 High Similarity NPC73875
0.8553 High Similarity NPC93662
0.8553 High Similarity NPC86305
0.8553 High Similarity NPC477925
0.8553 High Similarity NPC46160
0.8553 High Similarity NPC107059
0.8553 High Similarity NPC14112
0.8553 High Similarity NPC300324
0.8553 High Similarity NPC321381
0.8553 High Similarity NPC321016
0.8553 High Similarity NPC274079
0.8533 High Similarity NPC25511
0.8533 High Similarity NPC476366
0.8533 High Similarity NPC201048
0.8533 High Similarity NPC62657
0.8533 High Similarity NPC192638
0.8519 High Similarity NPC477578
0.8514 High Similarity NPC164022
0.8493 Intermediate Similarity NPC210323
0.8481 Intermediate Similarity NPC290495
0.8481 Intermediate Similarity NPC3915
0.8481 Intermediate Similarity NPC476646
0.8481 Intermediate Similarity NPC195334
0.8481 Intermediate Similarity NPC474531
0.8472 Intermediate Similarity NPC197805
0.8462 Intermediate Similarity NPC30986
0.8462 Intermediate Similarity NPC209430
0.8452 Intermediate Similarity NPC477872
0.8452 Intermediate Similarity NPC130278
0.8452 Intermediate Similarity NPC210037
0.8452 Intermediate Similarity NPC471432
0.8452 Intermediate Similarity NPC7260
0.8452 Intermediate Similarity NPC126369
0.8452 Intermediate Similarity NPC111110
0.8452 Intermediate Similarity NPC273621
0.8452 Intermediate Similarity NPC86372

  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 NPC34177 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
0.9726 High Similarity NPD7645 Phase 2
0.859 High Similarity NPD7525 Registered
0.8421 Intermediate Similarity NPD6942 Approved
0.8421 Intermediate Similarity NPD7339 Approved
0.8353 Intermediate Similarity NPD7515 Phase 2
0.8312 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD7748 Approved
0.7765 Intermediate Similarity NPD3618 Phase 1
0.7738 Intermediate Similarity NPD4786 Approved
0.7711 Intermediate Similarity NPD3667 Approved
0.7701 Intermediate Similarity NPD5328 Approved
0.7692 Intermediate Similarity NPD7902 Approved
0.7647 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD6924 Approved
0.7595 Intermediate Similarity NPD6926 Approved
0.7564 Intermediate Similarity NPD4243 Approved
0.7528 Intermediate Similarity NPD6079 Approved
0.75 Intermediate Similarity NPD8264 Approved
0.7407 Intermediate Similarity NPD6933 Approved
0.7375 Intermediate Similarity NPD4785 Approved
0.7375 Intermediate Similarity NPD4784 Approved
0.7363 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD7900 Approved
0.7342 Intermediate Similarity NPD7152 Approved
0.7342 Intermediate Similarity NPD7150 Approved
0.7342 Intermediate Similarity NPD7151 Approved
0.7326 Intermediate Similarity NPD3665 Phase 1
0.7326 Intermediate Similarity NPD3666 Approved
0.7326 Intermediate Similarity NPD3133 Approved
0.7308 Intermediate Similarity NPD6922 Approved
0.7308 Intermediate Similarity NPD6923 Approved
0.7273 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7509 Discontinued
0.7262 Intermediate Similarity NPD4748 Discontinued
0.7253 Intermediate Similarity NPD4202 Approved
0.7215 Intermediate Similarity NPD7143 Approved
0.7215 Intermediate Similarity NPD7144 Approved
0.7143 Intermediate Similarity NPD6929 Approved
0.7073 Intermediate Similarity NPD5275 Approved
0.7073 Intermediate Similarity NPD4190 Phase 3
0.7059 Intermediate Similarity NPD6931 Approved
0.7059 Intermediate Similarity NPD6930 Phase 2
0.7053 Intermediate Similarity NPD7638 Approved
0.7021 Intermediate Similarity NPD4697 Phase 3
0.7021 Intermediate Similarity NPD5221 Approved
0.7021 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD5222 Approved
0.6979 Remote Similarity NPD7639 Approved
0.6979 Remote Similarity NPD7640 Approved
0.6957 Remote Similarity NPD8034 Phase 2
0.6957 Remote Similarity NPD8035 Phase 2
0.6947 Remote Similarity NPD5173 Approved
0.6947 Remote Similarity NPD4755 Approved
0.6941 Remote Similarity NPD4195 Approved
0.6932 Remote Similarity NPD3668 Phase 3
0.6905 Remote Similarity NPD6932 Approved
0.6905 Remote Similarity NPD6925 Approved
0.6905 Remote Similarity NPD5776 Phase 2
0.6882 Remote Similarity NPD6399 Phase 3
0.6875 Remote Similarity NPD5290 Discontinued
0.6875 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6842 Remote Similarity NPD368 Approved
0.6824 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6824 Remote Similarity NPD7145 Approved
0.6818 Remote Similarity NPD6695 Phase 3
0.6813 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6804 Remote Similarity NPD5286 Approved
0.6804 Remote Similarity NPD4696 Approved
0.6804 Remote Similarity NPD5285 Approved
0.6804 Remote Similarity NPD4700 Approved
0.6778 Remote Similarity NPD5279 Phase 3
0.6744 Remote Similarity NPD6683 Phase 2
0.6742 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6739 Remote Similarity NPD4753 Phase 2
0.6739 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6735 Remote Similarity NPD5223 Approved
0.6705 Remote Similarity NPD4223 Phase 3
0.6705 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD5329 Approved
0.6667 Remote Similarity NPD6893 Approved
0.6667 Remote Similarity NPD7514 Phase 3
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD4695 Discontinued
0.6667 Remote Similarity NPD7332 Phase 2
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD5211 Phase 2
0.6634 Remote Similarity NPD6402 Approved
0.6634 Remote Similarity NPD7128 Approved
0.6634 Remote Similarity NPD5739 Approved
0.6634 Remote Similarity NPD6675 Approved
0.6629 Remote Similarity NPD4788 Approved
0.66 Remote Similarity NPD4754 Approved
0.66 Remote Similarity NPD5174 Approved
0.66 Remote Similarity NPD5175 Approved
0.6593 Remote Similarity NPD7334 Approved
0.6593 Remote Similarity NPD6409 Approved
0.6593 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6593 Remote Similarity NPD7521 Approved
0.6593 Remote Similarity NPD5330 Approved
0.6593 Remote Similarity NPD7146 Approved
0.6593 Remote Similarity NPD6684 Approved
0.6591 Remote Similarity NPD6902 Approved
0.6591 Remote Similarity NPD6898 Phase 1
0.6585 Remote Similarity NPD4787 Phase 1
0.6556 Remote Similarity NPD4197 Approved
0.6535 Remote Similarity NPD5141 Approved
0.6522 Remote Similarity NPD3573 Approved
0.6522 Remote Similarity NPD7524 Approved
0.6522 Remote Similarity NPD7750 Discontinued
0.6506 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6506 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6899 Approved
0.6505 Remote Similarity NPD6881 Approved
0.6505 Remote Similarity NPD7320 Approved
0.6486 Remote Similarity NPD342 Phase 1
0.6471 Remote Similarity NPD4767 Approved
0.6471 Remote Similarity NPD4768 Approved
0.6463 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6463 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6903 Approved
0.6442 Remote Similarity NPD6372 Approved
0.6442 Remote Similarity NPD6373 Approved
0.6437 Remote Similarity NPD3617 Approved
0.6429 Remote Similarity NPD6083 Phase 2
0.6429 Remote Similarity NPD6084 Phase 2
0.6421 Remote Similarity NPD6411 Approved
0.6413 Remote Similarity NPD4690 Approved
0.6413 Remote Similarity NPD4693 Phase 3
0.6413 Remote Similarity NPD4689 Approved
0.6413 Remote Similarity NPD4519 Discontinued
0.6413 Remote Similarity NPD5205 Approved
0.6413 Remote Similarity NPD4688 Approved
0.6413 Remote Similarity NPD4138 Approved
0.6413 Remote Similarity NPD4623 Approved
0.6408 Remote Similarity NPD5697 Approved
0.6408 Remote Similarity NPD5701 Approved
0.6395 Remote Similarity NPD6117 Approved
0.6392 Remote Similarity NPD5210 Approved
0.6392 Remote Similarity NPD4629 Approved
0.6383 Remote Similarity NPD6051 Approved
0.6381 Remote Similarity NPD7102 Approved
0.6381 Remote Similarity NPD6883 Approved
0.6381 Remote Similarity NPD7290 Approved
0.6364 Remote Similarity NPD4225 Approved
0.6353 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6011 Approved
0.6346 Remote Similarity NPD4730 Approved
0.6346 Remote Similarity NPD4729 Approved
0.6346 Remote Similarity NPD5168 Approved
0.6346 Remote Similarity NPD5128 Approved
0.6337 Remote Similarity NPD7632 Discontinued
0.6327 Remote Similarity NPD7614 Phase 1
0.6322 Remote Similarity NPD6116 Phase 1
0.6321 Remote Similarity NPD6649 Approved
0.6321 Remote Similarity NPD6617 Approved
0.6321 Remote Similarity NPD8130 Phase 1
0.6321 Remote Similarity NPD6869 Approved
0.6321 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6321 Remote Similarity NPD6650 Approved
0.6321 Remote Similarity NPD6847 Approved
0.6292 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6286 Remote Similarity NPD6014 Approved
0.6286 Remote Similarity NPD6012 Approved
0.6286 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6286 Remote Similarity NPD6013 Approved
0.6283 Remote Similarity NPD8328 Phase 3
0.6279 Remote Similarity NPD3703 Phase 2
0.6277 Remote Similarity NPD6672 Approved
0.6277 Remote Similarity NPD5737 Approved
0.6277 Remote Similarity NPD4722 Approved
0.6277 Remote Similarity NPD4723 Approved
0.6262 Remote Similarity NPD6882 Approved
0.6262 Remote Similarity NPD8297 Approved
0.625 Remote Similarity NPD6118 Approved
0.625 Remote Similarity NPD6115 Approved
0.625 Remote Similarity NPD6412 Phase 2
0.625 Remote Similarity NPD6697 Approved
0.625 Remote Similarity NPD7087 Discontinued
0.625 Remote Similarity NPD6114 Approved
0.6238 Remote Similarity NPD4159 Approved
0.6237 Remote Similarity NPD4694 Approved
0.6237 Remote Similarity NPD5690 Phase 2
0.6237 Remote Similarity NPD5280 Approved
0.6226 Remote Similarity NPD5249 Phase 3
0.6226 Remote Similarity NPD5251 Approved
0.6226 Remote Similarity NPD5135 Approved
0.6226 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6226 Remote Similarity NPD4634 Approved
0.6226 Remote Similarity NPD5247 Approved
0.6226 Remote Similarity NPD5248 Approved
0.6226 Remote Similarity NPD5169 Approved
0.6226 Remote Similarity NPD5250 Approved
0.6211 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6211 Remote Similarity NPD6101 Approved
0.619 Remote Similarity NPD4244 Approved
0.619 Remote Similarity NPD4245 Approved
0.6182 Remote Similarity NPD7115 Discovery
0.6182 Remote Similarity NPD8295 Clinical (unspecified phase)

  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