NPASS Compound

Structure

NPC169888 OpenBabel07101718312D 47 50 0 0 1 0 0 0 0 0999 V2000 1.5164 -10.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2901 -2.8697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3577 0.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0334 -3.1549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1379 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0036 -1.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0185 -0.2471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7792 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9402 -9.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3389 -8.5287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 -7.7355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1614 -6.8399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5852 -6.0468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9839 -5.1511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3577 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5087 -3.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3577 -1.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3577 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2068 -0.1157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6346 -4.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8371 1.6888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3577 -1.5863 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7815 -0.7932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9590 -5.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -3.6628 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7815 -3.3599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6596 -1.5863 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0834 -3.3599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0834 -0.7932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7815 0.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6596 -2.5667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5087 -1.0961 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8490 0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0558 0.3745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2109 -4.8437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4134 2.4819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -5.8418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -4.6432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0844 1.7256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9989 -0.2471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2068 -1.0961 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6596 -4.1530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2359 0.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3577 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3577 -4.1530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 8 33 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 31 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 35 2 0 0 0 0 19 42 1 0 0 0 0 20 36 2 0 0 0 0 20 43 1 0 0 0 0 21 37 2 0 0 0 0 21 44 1 0 0 0 0 22 32 1 1 0 0 0 22 42 1 0 0 0 0 23 34 1 1 0 0 0 23 45 1 0 0 0 0 24 38 2 0 0 0 0 24 46 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 25 39 1 1 0 0 0 26 46 1 6 0 0 0 27 29 1 0 0 0 0 27 31 1 6 0 0 0 27 32 1 0 0 0 0 28 31 1 6 0 0 0 28 43 1 0 0 0 0 29 34 1 1 0 0 0 29 44 1 0 0 0 0 30 33 1 0 0 0 0 30 40 2 0 0 0 0 30 45 1 0 0 0 0 31 6 1 6 0 0 0 32 7 1 6 0 0 0 32 41 1 0 0 0 0 33 34 1 6 0 0 0 33 47 1 0 0 0 0 34 47 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.31
Volume:	658.212
LogP:	4.029
LogD:	2.205
LogS:	-4.124
# Rotatable Bonds:	14
TPSA:	184.49
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	6.34
Fsp3:	0.735
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.268
MDCK Permeability:	0.00015705148689448833
Pgp-inhibitor:	1.0
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.4
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	72.47335052490234%
Volume Distribution (VD):	1.326
Pgp-substrate:	22.113210678100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.796
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	2.824
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.392
Carcinogencity:	0.057
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC169888

Natural Product ID:	NPC169888
*Common Name:**	Briarlide D
IUPAC Name:	n.a.
Synonyms:	Briarlide D
Standard InCHIKey:	FLOSHVVWPCFVPS-JNTBWSLFSA-N
Standard InCHI:	InChI=1S/C34H48O13/c1-9-10-11-12-13-14-24(38)46-26-18(2)17-23-34(33(8,47-34)30(40)45-23)29(44-21(5)37)27-31(6,28(25(26)39)43-20(4)36)16-15-22(32(27,7)41)42-19(3)35/h15-17,22-23,25-29,39,41H,9-14H2,1-8H3/b18-17-/t22-,23+,25-,26+,27-,28+,29-,31+,32-,33+,34+/m1/s1
SMILES:	CCCCCCCC(=O)O[C@H]1/C(=C[C@@H]2OC(=O)[C@]3([C@@]2(O3)[C@@H]([C@@H]2[C@]([C@H]([C@@H]1O)OC(=O)C)(C)C=C[C@H]([C@@]2(C)O)OC(=O)C)OC(=O)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503995
PubChem CID:	11445242
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640510]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Formosan gorgonian	n.a.	PMID[8984161]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Indonesian Gorgonian	n.a.	PMID[9548870]

☑ 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

Activity Type	# Activity
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	2.26	ug.mL-1	PMID[484538]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	=	2.49	ug.mL-1	PMID[484538]

☑ 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 NPC169888 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1342
0.2-0.3	4678
0.3-0.4	9652
0.4-0.5	13096
0.5-0.6	7650
0.6-0.7	4820
0.7-0.8	1091
0.8-0.85	100
0.85-0.9	21
0.9-0.95	7
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC327286
1.0	High Similarity	NPC55972
0.99	High Similarity	NPC15218
0.9899	High Similarity	NPC324327
0.9899	High Similarity	NPC474421
0.9899	High Similarity	NPC326994
0.9899	High Similarity	NPC194620
0.9899	High Similarity	NPC72813
0.98	High Similarity	NPC14862
0.98	High Similarity	NPC474664
0.98	High Similarity	NPC233379
0.9798	High Similarity	NPC16313
0.9798	High Similarity	NPC9303
0.96	High Similarity	NPC475802
0.9596	High Similarity	NPC4620
0.951	High Similarity	NPC475922
0.95	High Similarity	NPC220964
0.95	High Similarity	NPC475676
0.9417	High Similarity	NPC161816
0.9417	High Similarity	NPC115257
0.9057	High Similarity	NPC473877
0.902	High Similarity	NPC69171
0.902	High Similarity	NPC474166
0.902	High Similarity	NPC474165
0.902	High Similarity	NPC19239
0.8922	High Similarity	NPC183571
0.8807	High Similarity	NPC474333
0.8774	High Similarity	NPC42662
0.8738	High Similarity	NPC471148
0.8727	High Similarity	NPC296822
0.8679	High Similarity	NPC473939
0.8679	High Similarity	NPC473595
0.8679	High Similarity	NPC94377
0.8641	High Similarity	NPC474339
0.8641	High Similarity	NPC164598
0.8585	High Similarity	NPC475587
0.8585	High Similarity	NPC475510
0.8585	High Similarity	NPC477513
0.8571	High Similarity	NPC472756
0.8558	High Similarity	NPC472754
0.8545	High Similarity	NPC73314
0.8544	High Similarity	NPC475949
0.8532	High Similarity	NPC317687
0.8519	High Similarity	NPC281624
0.8462	Intermediate Similarity	NPC472753
0.844	Intermediate Similarity	NPC317107
0.8393	Intermediate Similarity	NPC476713
0.8393	Intermediate Similarity	NPC476712
0.8381	Intermediate Similarity	NPC149371
0.835	Intermediate Similarity	NPC471140
0.8349	Intermediate Similarity	NPC473843
0.8349	Intermediate Similarity	NPC473975
0.8349	Intermediate Similarity	NPC473594
0.8349	Intermediate Similarity	NPC474586
0.8304	Intermediate Similarity	NPC476711
0.8304	Intermediate Similarity	NPC476710
0.8302	Intermediate Similarity	NPC472755
0.8286	Intermediate Similarity	NPC47880
0.8273	Intermediate Similarity	NPC194619
0.8269	Intermediate Similarity	NPC471144
0.8252	Intermediate Similarity	NPC473859
0.8252	Intermediate Similarity	NPC230800
0.8252	Intermediate Similarity	NPC279621
0.8246	Intermediate Similarity	NPC470186
0.8224	Intermediate Similarity	NPC474741
0.8224	Intermediate Similarity	NPC472748
0.819	Intermediate Similarity	NPC288876
0.8165	Intermediate Similarity	NPC322903
0.8158	Intermediate Similarity	NPC475401
0.8155	Intermediate Similarity	NPC475659
0.8148	Intermediate Similarity	NPC472751
0.8148	Intermediate Similarity	NPC472749
0.8131	Intermediate Similarity	NPC475871
0.8131	Intermediate Similarity	NPC472747
0.8131	Intermediate Similarity	NPC472750
0.8131	Intermediate Similarity	NPC475945
0.8113	Intermediate Similarity	NPC477511
0.8113	Intermediate Similarity	NPC201718
0.8113	Intermediate Similarity	NPC264477
0.8095	Intermediate Similarity	NPC161855
0.8095	Intermediate Similarity	NPC222303
0.8087	Intermediate Similarity	NPC477092
0.8081	Intermediate Similarity	NPC478112
0.8077	Intermediate Similarity	NPC476315
0.8077	Intermediate Similarity	NPC17585
0.8073	Intermediate Similarity	NPC26617
0.807	Intermediate Similarity	NPC471146
0.807	Intermediate Similarity	NPC475305
0.8058	Intermediate Similarity	NPC474247
0.8056	Intermediate Similarity	NPC258532
0.8056	Intermediate Similarity	NPC477510
0.8056	Intermediate Similarity	NPC471143
0.8037	Intermediate Similarity	NPC474747
0.802	Intermediate Similarity	NPC475971
0.8019	Intermediate Similarity	NPC477512
0.8018	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC475130
0.8	Intermediate Similarity	NPC308191
0.8	Intermediate Similarity	NPC474286
0.7982	Intermediate Similarity	NPC270478
0.7981	Intermediate Similarity	NPC471141
0.7981	Intermediate Similarity	NPC107476
0.7981	Intermediate Similarity	NPC270013
0.7981	Intermediate Similarity	NPC14961
0.7981	Intermediate Similarity	NPC36954
0.7966	Intermediate Similarity	NPC303006
0.7965	Intermediate Similarity	NPC477126
0.7965	Intermediate Similarity	NPC469463
0.7965	Intermediate Similarity	NPC469454
0.7965	Intermediate Similarity	NPC469496
0.7963	Intermediate Similarity	NPC475321
0.7961	Intermediate Similarity	NPC475838
0.7961	Intermediate Similarity	NPC476300
0.7961	Intermediate Similarity	NPC212486
0.7961	Intermediate Similarity	NPC125674
0.7961	Intermediate Similarity	NPC228451
0.7951	Intermediate Similarity	NPC470185
0.7946	Intermediate Similarity	NPC287311
0.7944	Intermediate Similarity	NPC474742
0.7944	Intermediate Similarity	NPC476270
0.7925	Intermediate Similarity	NPC473326
0.7913	Intermediate Similarity	NPC473590
0.7905	Intermediate Similarity	NPC158416
0.7905	Intermediate Similarity	NPC473291
0.7905	Intermediate Similarity	NPC39859
0.7905	Intermediate Similarity	NPC470883
0.7905	Intermediate Similarity	NPC54731
0.7905	Intermediate Similarity	NPC76862
0.789	Intermediate Similarity	NPC203659
0.789	Intermediate Similarity	NPC146731
0.789	Intermediate Similarity	NPC296950
0.7885	Intermediate Similarity	NPC474035
0.7885	Intermediate Similarity	NPC81386
0.7885	Intermediate Similarity	NPC303942
0.7885	Intermediate Similarity	NPC57405
0.7881	Intermediate Similarity	NPC310035
0.7881	Intermediate Similarity	NPC282003
0.7881	Intermediate Similarity	NPC188222
0.787	Intermediate Similarity	NPC105725
0.787	Intermediate Similarity	NPC320019
0.787	Intermediate Similarity	NPC283567
0.787	Intermediate Similarity	NPC324017
0.787	Intermediate Similarity	NPC474709
0.787	Intermediate Similarity	NPC473596
0.7864	Intermediate Similarity	NPC30515
0.7864	Intermediate Similarity	NPC184463
0.7863	Intermediate Similarity	NPC475003
0.7857	Intermediate Similarity	NPC472215
0.7857	Intermediate Similarity	NPC475134
0.7857	Intermediate Similarity	NPC475563
0.7857	Intermediate Similarity	NPC472214
0.783	Intermediate Similarity	NPC40812
0.7822	Intermediate Similarity	NPC266957
0.7818	Intermediate Similarity	NPC179891
0.7815	Intermediate Similarity	NPC67251
0.781	Intermediate Similarity	NPC471142
0.7807	Intermediate Similarity	NPC101965
0.7807	Intermediate Similarity	NPC101400
0.7798	Intermediate Similarity	NPC474783
0.7798	Intermediate Similarity	NPC232515
0.7798	Intermediate Similarity	NPC260809
0.7798	Intermediate Similarity	NPC110989
0.7788	Intermediate Similarity	NPC126897
0.7788	Intermediate Similarity	NPC475912
0.7788	Intermediate Similarity	NPC297945
0.7788	Intermediate Similarity	NPC475668
0.7788	Intermediate Similarity	NPC473921
0.7788	Intermediate Similarity	NPC179798
0.7788	Intermediate Similarity	NPC475480
0.7788	Intermediate Similarity	NPC304180
0.7778	Intermediate Similarity	NPC231601
0.7778	Intermediate Similarity	NPC473332
0.7778	Intermediate Similarity	NPC15993
0.7768	Intermediate Similarity	NPC477102
0.7767	Intermediate Similarity	NPC469368
0.7767	Intermediate Similarity	NPC475855
0.7767	Intermediate Similarity	NPC474232
0.7767	Intermediate Similarity	NPC475748
0.7767	Intermediate Similarity	NPC65359
0.7767	Intermediate Similarity	NPC51004
0.7759	Intermediate Similarity	NPC471145
0.7759	Intermediate Similarity	NPC469684
0.7748	Intermediate Similarity	NPC266514
0.7745	Intermediate Similarity	NPC287089
0.7745	Intermediate Similarity	NPC201046
0.7745	Intermediate Similarity	NPC476803
0.7739	Intermediate Similarity	NPC138303
0.7739	Intermediate Similarity	NPC67290
0.7739	Intermediate Similarity	NPC133677
0.7736	Intermediate Similarity	NPC476009
0.7731	Intermediate Similarity	NPC470265
0.7731	Intermediate Similarity	NPC23786
0.7723	Intermediate Similarity	NPC278283
0.7723	Intermediate Similarity	NPC50637
0.7719	Intermediate Similarity	NPC473522
0.7719	Intermediate Similarity	NPC475277
0.7719	Intermediate Similarity	NPC477093
0.7719	Intermediate Similarity	NPC313921
0.7719	Intermediate Similarity	NPC98038
0.7719	Intermediate Similarity	NPC66108

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 NPC169888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1867
0.2-0.3	3703
0.3-0.4	2240
0.4-0.5	703
0.5-0.6	305
0.6-0.7	122
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8073	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6698	Approved
0.7941	Intermediate Similarity	NPD46	Approved
0.7788	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6371	Approved
0.7692	Intermediate Similarity	NPD7983	Approved
0.7596	Intermediate Similarity	NPD7838	Discovery
0.7383	Intermediate Similarity	NPD5282	Discontinued
0.7355	Intermediate Similarity	NPD8515	Approved
0.7355	Intermediate Similarity	NPD8517	Approved
0.7355	Intermediate Similarity	NPD8513	Phase 3
0.7355	Intermediate Similarity	NPD8516	Approved
0.7311	Intermediate Similarity	NPD7115	Discovery
0.7282	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6686	Approved
0.7156	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5779	Approved
0.713	Intermediate Similarity	NPD5778	Approved
0.7117	Intermediate Similarity	NPD4225	Approved
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8074	Phase 3
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6319	Approved
0.6991	Remote Similarity	NPD5344	Discontinued
0.6964	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5785	Approved
0.6885	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6411	Approved
0.6852	Remote Similarity	NPD1695	Approved
0.685	Remote Similarity	NPD8273	Phase 1
0.6842	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8297	Approved
0.6825	Remote Similarity	NPD8328	Phase 3
0.6786	Remote Similarity	NPD7839	Suspended
0.6772	Remote Similarity	NPD7492	Approved
0.6744	Remote Similarity	NPD7736	Approved
0.6731	Remote Similarity	NPD5369	Approved
0.6727	Remote Similarity	NPD7637	Suspended
0.672	Remote Similarity	NPD6054	Approved
0.6719	Remote Similarity	NPD6616	Approved
0.6697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6101	Approved
0.6695	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6614	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD6649	Approved
0.6612	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6648	Approved
0.6604	Remote Similarity	NPD7154	Phase 3
0.6589	Remote Similarity	NPD8451	Approved
0.6587	Remote Similarity	NPD6059	Approved
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6579	Remote Similarity	NPD6083	Phase 2
0.6579	Remote Similarity	NPD6084	Phase 2
0.6574	Remote Similarity	NPD4249	Approved
0.6574	Remote Similarity	NPD5786	Approved
0.6565	Remote Similarity	NPD7319	Approved
0.6562	Remote Similarity	NPD7642	Approved
0.6562	Remote Similarity	NPD7829	Approved
0.6562	Remote Similarity	NPD7830	Approved
0.6557	Remote Similarity	NPD6053	Discontinued
0.6538	Remote Similarity	NPD8448	Approved
0.6535	Remote Similarity	NPD6921	Approved
0.6535	Remote Similarity	NPD6015	Approved
0.6535	Remote Similarity	NPD6016	Approved
0.6522	Remote Similarity	NPD7638	Approved
0.6518	Remote Similarity	NPD6399	Phase 3
0.6504	Remote Similarity	NPD8133	Approved
0.6504	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD6881	Approved
0.6484	Remote Similarity	NPD5988	Approved
0.6481	Remote Similarity	NPD5363	Approved
0.6481	Remote Similarity	NPD1694	Approved
0.6476	Remote Similarity	NPD4821	Approved
0.6476	Remote Similarity	NPD4252	Approved
0.6476	Remote Similarity	NPD4820	Approved
0.6476	Remote Similarity	NPD4819	Approved
0.6476	Remote Similarity	NPD4822	Approved
0.6476	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD8039	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6466	Remote Similarity	NPD7260	Phase 2
0.6466	Remote Similarity	NPD7640	Approved
0.6466	Remote Similarity	NPD7639	Approved
0.6462	Remote Similarity	NPD7507	Approved
0.6449	Remote Similarity	NPD5362	Discontinued
0.6449	Remote Similarity	NPD6110	Phase 1
0.6446	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7604	Phase 2
0.6423	Remote Similarity	NPD6882	Approved
0.6417	Remote Similarity	NPD6412	Phase 2
0.6417	Remote Similarity	NPD5697	Approved
0.6406	Remote Similarity	NPD8444	Approved
0.6404	Remote Similarity	NPD5695	Phase 3
0.6393	Remote Similarity	NPD7102	Approved
0.6393	Remote Similarity	NPD7290	Approved
0.6393	Remote Similarity	NPD6883	Approved
0.6391	Remote Similarity	NPD8391	Approved
0.6391	Remote Similarity	NPD8390	Approved
0.6391	Remote Similarity	NPD8392	Approved
0.6385	Remote Similarity	NPD8340	Approved
0.6385	Remote Similarity	NPD8342	Approved
0.6385	Remote Similarity	NPD8341	Approved
0.6385	Remote Similarity	NPD8299	Approved
0.6379	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD7320	Approved
0.6355	Remote Similarity	NPD6435	Approved
0.6349	Remote Similarity	NPD6009	Approved
0.6341	Remote Similarity	NPD6847	Approved
0.6341	Remote Similarity	NPD6869	Approved
0.6341	Remote Similarity	NPD6617	Approved
0.6333	Remote Similarity	NPD6008	Approved
0.633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.6286	Remote Similarity	NPD4271	Approved
0.6286	Remote Similarity	NPD4268	Approved
0.6281	Remote Similarity	NPD5701	Approved
0.6279	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8033	Approved
0.6279	Remote Similarity	NPD7503	Approved
0.6279	Remote Similarity	NPD5983	Phase 2
0.626	Remote Similarity	NPD4634	Approved
0.6231	Remote Similarity	NPD8080	Discontinued
0.623	Remote Similarity	NPD6011	Approved
0.6216	Remote Similarity	NPD7524	Approved
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD2204	Approved
0.6207	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5209	Approved
0.6204	Remote Similarity	NPD8415	Approved
0.6204	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8377	Approved
0.6202	Remote Similarity	NPD8294	Approved
0.6176	Remote Similarity	NPD6845	Suspended
0.6172	Remote Similarity	NPD7328	Approved
0.6172	Remote Similarity	NPD7327	Approved
0.6168	Remote Similarity	NPD5368	Approved
0.6161	Remote Similarity	NPD5737	Approved
0.6161	Remote Similarity	NPD6672	Approved
0.6159	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8380	Approved
0.6154	Remote Similarity	NPD8296	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD8335	Approved
0.6154	Remote Similarity	NPD8378	Approved
0.6154	Remote Similarity	NPD8379	Approved
0.6148	Remote Similarity	NPD5956	Approved
0.614	Remote Similarity	NPD5693	Phase 1
0.6129	Remote Similarity	NPD6421	Discontinued
0.6124	Remote Similarity	NPD7516	Approved
0.6119	Remote Similarity	NPD6033	Approved
0.6094	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1700	Approved
0.6	Remote Similarity	NPD5331	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD5332	Approved
0.5984	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5210	Approved
0.5983	Remote Similarity	NPD4629	Approved
0.5982	Remote Similarity	NPD6098	Approved
0.5969	Remote Similarity	NPD7500	Approved
0.5965	Remote Similarity	NPD5370	Suspended
0.5965	Remote Similarity	NPD6673	Approved
0.5965	Remote Similarity	NPD6904	Approved
0.5965	Remote Similarity	NPD6080	Approved
0.5965	Remote Similarity	NPD4753	Phase 2
0.5963	Remote Similarity	NPD4790	Discontinued
0.596	Remote Similarity	NPD3197	Phase 1
0.595	Remote Similarity	NPD5211	Phase 2
0.595	Remote Similarity	NPD7632	Discontinued
0.5946	Remote Similarity	NPD4786	Approved
0.5929	Remote Similarity	NPD7750	Discontinued
0.5923	Remote Similarity	NPD6335	Approved
0.5923	Remote Similarity	NPD7641	Discontinued
0.5917	Remote Similarity	NPD5286	Approved
0.5917	Remote Similarity	NPD4696	Approved
0.5917	Remote Similarity	NPD5285	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