NPASS Compound

Structure

CID162033 OpenBabel06191715532D 42 46 0 0 1 0 0 0 0 0999 V2000 3.3290 -3.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7789 -2.6982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6446 6.2069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5246 5.6990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7958 2.7033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2479 1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2479 4.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5759 -0.9082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1517 -1.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9744 -0.0133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0972 4.7003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9466 5.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5504 2.2493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9465 2.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4933 3.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6445 3.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5505 3.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0972 1.7589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7532 -2.5958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3985 0.7793 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3986 1.7589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9465 3.2293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0972 3.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6968 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7959 4.7003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4933 4.7002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6968 0.9797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8484 1.4695 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4243 0.6769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6446 5.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7958 3.7196 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2479 2.2493 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2479 3.2293 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5452 -0.4898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3593 5.2002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5452 1.4695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 2.4492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0258 -0.2181 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 0.8484 1.4695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 6 34 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 33 1 0 0 0 0 17 35 1 0 0 0 0 18 34 1 0 0 0 0 19 25 1 0 0 0 0 19 41 1 0 0 0 0 21 10 1 1 0 0 0 21 22 1 0 0 0 0 21 30 1 0 0 0 0 22 34 1 1 0 0 0 23 24 2 0 0 0 0 23 33 1 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 25 36 1 1 0 0 0 26 32 1 0 0 0 0 26 33 1 1 0 0 0 27 32 1 0 0 0 0 27 37 2 0 0 0 0 28 29 1 0 0 0 0 28 38 1 6 0 0 0 29 31 1 0 0 0 0 29 39 1 1 0 0 0 30 40 2 0 0 0 0 30 42 1 0 0 0 0 31 41 1 0 0 0 0 31 42 1 6 0 0 0 33 5 1 1 0 0 0 34 35 1 1 0 0 0 35 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.39
Volume:	622.119
LogP:	4.893
LogD:	3.937
LogS:	-4.915
# Rotatable Bonds:	7
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	5.271
Fsp3:	0.829
Lipinski Rule-of-5:	Accepted
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:	-5.166
MDCK Permeability:	1.1947241546295118e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.59
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	92.95747375488281%
Volume Distribution (VD):	1.437
Pgp-substrate:	2.1909139156341553%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	3.372
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.305
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.675
Skin Sensitization:	0.155
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC162033

Natural Product ID:	NPC162033
*Common Name:**	Fomitoside C
IUPAC Name:	[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] (2R)-6-methyl-2-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoate
Synonyms:	Fomitoside C
Standard InCHIKey:	FTPANSKMWIDRLL-QDVPQEPLSA-N
Standard InCHI:	InChI=1S/C35H54O7/c1-20(2)9-8-10-21(30(40)42-31-29(39)28(38)25(36)19-41-31)22-13-17-35(7)24-11-12-26-32(3,4)27(37)15-16-33(26,5)23(24)14-18-34(22,35)6/h9,21-22,25-26,28-29,31,36,38-39H,8,10-19H2,1-7H3/t21-,22-,25-,26+,28+,29-,31+,33-,34-,35+/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C(=O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510510
PubChem CID:	11284735
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
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	fruit bodies	Tokushima, Japan	1999-Autumn	PMID[15679320]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26925	Fomitopsis pinicola	Species	Fomitopsidaceae	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

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	1910000.0	nM	PMID[558224]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	5110000.0	nM	PMID[558224]

☑ 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 NPC162033 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	203
0.1-0.2	1196
0.2-0.3	4857
0.3-0.4	11943
0.4-0.5	9423
0.5-0.6	5847
0.6-0.7	5761
0.7-0.8	3243
0.8-0.85	147
0.85-0.9	60
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC223741
0.9505	High Similarity	NPC265655
0.9412	High Similarity	NPC114961
0.9412	High Similarity	NPC27551
0.9412	High Similarity	NPC129340
0.9406	High Similarity	NPC195708
0.9406	High Similarity	NPC295389
0.9327	High Similarity	NPC73455
0.9327	High Similarity	NPC200944
0.932	High Similarity	NPC292196
0.9143	High Similarity	NPC251309
0.9135	High Similarity	NPC250481
0.9135	High Similarity	NPC285410
0.9135	High Similarity	NPC263827
0.9126	High Similarity	NPC118225
0.9126	High Similarity	NPC246205
0.9057	High Similarity	NPC473882
0.9057	High Similarity	NPC220293
0.9057	High Similarity	NPC116024
0.9048	High Similarity	NPC233003
0.9038	High Similarity	NPC475317
0.9038	High Similarity	NPC154856
0.9038	High Similarity	NPC52241
0.902	High Similarity	NPC95243
0.902	High Similarity	NPC210178
0.902	High Similarity	NPC63023
0.8942	High Similarity	NPC477070
0.8942	High Similarity	NPC477069
0.8922	High Similarity	NPC121566
0.8922	High Similarity	NPC100955
0.8911	High Similarity	NPC94919
0.89	High Similarity	NPC167974
0.8868	High Similarity	NPC474265
0.8868	High Similarity	NPC210420
0.8868	High Similarity	NPC130427
0.8857	High Similarity	NPC101450
0.8812	High Similarity	NPC21064
0.8812	High Similarity	NPC121072
0.8796	High Similarity	NPC244127
0.8785	High Similarity	NPC477944
0.8785	High Similarity	NPC260665
0.8774	High Similarity	NPC477073
0.8774	High Similarity	NPC269466
0.8762	High Similarity	NPC137917
0.875	High Similarity	NPC283849
0.8739	High Similarity	NPC202051
0.8725	High Similarity	NPC154452
0.8704	High Similarity	NPC74727
0.8704	High Similarity	NPC474557
0.8679	High Similarity	NPC78046
0.8679	High Similarity	NPC220984
0.8679	High Similarity	NPC269095
0.8667	High Similarity	NPC476123
0.8667	High Similarity	NPC28198
0.8667	High Similarity	NPC284807
0.8667	High Similarity	NPC177246
0.8649	High Similarity	NPC471406
0.8636	High Similarity	NPC239293
0.8624	High Similarity	NPC279638
0.8611	High Similarity	NPC477074
0.8585	High Similarity	NPC167383
0.8585	High Similarity	NPC306746
0.8585	High Similarity	NPC127853
0.8585	High Similarity	NPC57362
0.8585	High Similarity	NPC204407
0.8585	High Similarity	NPC237503
0.8571	High Similarity	NPC287269
0.8571	High Similarity	NPC473538
0.8571	High Similarity	NPC293512
0.8571	High Similarity	NPC475182
0.8532	High Similarity	NPC165439
0.8519	High Similarity	NPC471967
0.8519	High Similarity	NPC477253
0.8515	High Similarity	NPC473890
0.8515	High Similarity	NPC243728
0.8505	High Similarity	NPC110139
0.8505	High Similarity	NPC29069
0.8505	High Similarity	NPC56713
0.8505	High Similarity	NPC136877
0.8505	High Similarity	NPC274507
0.8505	High Similarity	NPC476885
0.8505	High Similarity	NPC174679
0.8505	High Similarity	NPC68419
0.8505	High Similarity	NPC476882
0.8505	High Similarity	NPC279554
0.8505	High Similarity	NPC474589
0.8505	High Similarity	NPC102914
0.8505	High Similarity	NPC476881
0.8505	High Similarity	NPC59804
0.8505	High Similarity	NPC108709
0.8505	High Similarity	NPC476884
0.8505	High Similarity	NPC164194
0.8505	High Similarity	NPC90856
0.8505	High Similarity	NPC199457
0.8505	High Similarity	NPC7870
0.8505	High Similarity	NPC127056
0.8505	High Similarity	NPC242611
0.8505	High Similarity	NPC476886
0.8505	High Similarity	NPC475296
0.8505	High Similarity	NPC476880
0.8505	High Similarity	NPC476883
0.8505	High Similarity	NPC476887
0.8505	High Similarity	NPC270667
0.8505	High Similarity	NPC75747
0.85	High Similarity	NPC108141
0.8496	Intermediate Similarity	NPC156789
0.8491	Intermediate Similarity	NPC88744
0.8491	Intermediate Similarity	NPC224414
0.8491	Intermediate Similarity	NPC295980
0.8491	Intermediate Similarity	NPC258323
0.8476	Intermediate Similarity	NPC475611
0.8476	Intermediate Similarity	NPC473199
0.8469	Intermediate Similarity	NPC219495
0.8468	Intermediate Similarity	NPC86020
0.8468	Intermediate Similarity	NPC291564
0.8468	Intermediate Similarity	NPC475632
0.8455	Intermediate Similarity	NPC31797
0.8431	Intermediate Similarity	NPC56071
0.8431	Intermediate Similarity	NPC158088
0.8431	Intermediate Similarity	NPC70733
0.8426	Intermediate Similarity	NPC191763
0.8426	Intermediate Similarity	NPC108748
0.8426	Intermediate Similarity	NPC211798
0.8426	Intermediate Similarity	NPC297208
0.8426	Intermediate Similarity	NPC473481
0.8426	Intermediate Similarity	NPC190837
0.8426	Intermediate Similarity	NPC235841
0.8426	Intermediate Similarity	NPC179434
0.8426	Intermediate Similarity	NPC31839
0.8426	Intermediate Similarity	NPC30397
0.8426	Intermediate Similarity	NPC164419
0.8421	Intermediate Similarity	NPC160084
0.8416	Intermediate Similarity	NPC207617
0.8411	Intermediate Similarity	NPC240125
0.8411	Intermediate Similarity	NPC473844
0.8411	Intermediate Similarity	NPC51947
0.8411	Intermediate Similarity	NPC91583
0.8407	Intermediate Similarity	NPC42675
0.8396	Intermediate Similarity	NPC234160
0.8393	Intermediate Similarity	NPC477071
0.8393	Intermediate Similarity	NPC232258
0.8393	Intermediate Similarity	NPC319570
0.8393	Intermediate Similarity	NPC161738
0.8381	Intermediate Similarity	NPC85593
0.8381	Intermediate Similarity	NPC31430
0.8365	Intermediate Similarity	NPC473928
0.8364	Intermediate Similarity	NPC477580
0.8364	Intermediate Similarity	NPC471398
0.835	Intermediate Similarity	NPC469942
0.835	Intermediate Similarity	NPC282669
0.8349	Intermediate Similarity	NPC139044
0.8349	Intermediate Similarity	NPC256798
0.8349	Intermediate Similarity	NPC101744
0.8349	Intermediate Similarity	NPC109079
0.8349	Intermediate Similarity	NPC195132
0.8349	Intermediate Similarity	NPC10320
0.8349	Intermediate Similarity	NPC471383
0.8349	Intermediate Similarity	NPC48249
0.8349	Intermediate Similarity	NPC1046
0.8349	Intermediate Similarity	NPC46388
0.8349	Intermediate Similarity	NPC100383
0.8349	Intermediate Similarity	NPC475516
0.8349	Intermediate Similarity	NPC116794
0.8349	Intermediate Similarity	NPC212968
0.8349	Intermediate Similarity	NPC79718
0.8349	Intermediate Similarity	NPC104400
0.8349	Intermediate Similarity	NPC469946
0.8349	Intermediate Similarity	NPC292677
0.8349	Intermediate Similarity	NPC324875
0.8349	Intermediate Similarity	NPC475504
0.8349	Intermediate Similarity	NPC65590
0.8349	Intermediate Similarity	NPC37739
0.8349	Intermediate Similarity	NPC104071
0.8349	Intermediate Similarity	NPC276093
0.8349	Intermediate Similarity	NPC64106
0.8349	Intermediate Similarity	NPC128925
0.8349	Intermediate Similarity	NPC473373
0.8349	Intermediate Similarity	NPC473383
0.8349	Intermediate Similarity	NPC139894
0.8349	Intermediate Similarity	NPC257468
0.8349	Intermediate Similarity	NPC125923
0.8349	Intermediate Similarity	NPC102439
0.8349	Intermediate Similarity	NPC161434
0.8349	Intermediate Similarity	NPC80843
0.8348	Intermediate Similarity	NPC318135
0.8348	Intermediate Similarity	NPC473474
0.8348	Intermediate Similarity	NPC130229
0.8348	Intermediate Similarity	NPC248202
0.8333	Intermediate Similarity	NPC127153
0.8333	Intermediate Similarity	NPC83005
0.8333	Intermediate Similarity	NPC106760
0.8319	Intermediate Similarity	NPC129393
0.8319	Intermediate Similarity	NPC470312
0.8319	Intermediate Similarity	NPC475187
0.8319	Intermediate Similarity	NPC472257
0.8318	Intermediate Similarity	NPC473288
0.8318	Intermediate Similarity	NPC230888
0.8318	Intermediate Similarity	NPC272576
0.8318	Intermediate Similarity	NPC472988
0.8318	Intermediate Similarity	NPC38217

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 NPC162033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1518
0.2-0.3	4070
0.3-0.4	2245
0.4-0.5	605
0.5-0.6	210
0.6-0.7	221
0.7-0.8	108
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8932	High Similarity	NPD6412	Phase 2
0.8411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6686	Approved
0.7946	Intermediate Similarity	NPD8133	Approved
0.7941	Intermediate Similarity	NPD6399	Phase 3
0.7833	Intermediate Similarity	NPD7736	Approved
0.7815	Intermediate Similarity	NPD7507	Approved
0.7797	Intermediate Similarity	NPD8328	Phase 3
0.775	Intermediate Similarity	NPD8293	Discontinued
0.7642	Intermediate Similarity	NPD6083	Phase 2
0.7642	Intermediate Similarity	NPD6084	Phase 2
0.7623	Intermediate Similarity	NPD7319	Approved
0.7619	Intermediate Similarity	NPD5695	Phase 3
0.7586	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD6370	Approved
0.7544	Intermediate Similarity	NPD8297	Approved
0.7544	Intermediate Similarity	NPD6882	Approved
0.7542	Intermediate Similarity	NPD8377	Approved
0.7542	Intermediate Similarity	NPD8294	Approved
0.7521	Intermediate Similarity	NPD7328	Approved
0.7521	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.7479	Intermediate Similarity	NPD8380	Approved
0.7479	Intermediate Similarity	NPD8335	Approved
0.7479	Intermediate Similarity	NPD7503	Approved
0.7479	Intermediate Similarity	NPD8379	Approved
0.7479	Intermediate Similarity	NPD8378	Approved
0.7479	Intermediate Similarity	NPD8296	Approved
0.7479	Intermediate Similarity	NPD8033	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7458	Intermediate Similarity	NPD7516	Approved
0.7438	Intermediate Similarity	NPD7492	Approved
0.7436	Intermediate Similarity	NPD6009	Approved
0.7395	Intermediate Similarity	NPD6054	Approved
0.7395	Intermediate Similarity	NPD6059	Approved
0.7379	Intermediate Similarity	NPD5737	Approved
0.7379	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6672	Approved
0.7377	Intermediate Similarity	NPD6616	Approved
0.7358	Intermediate Similarity	NPD7748	Approved
0.7353	Intermediate Similarity	NPD6684	Approved
0.7353	Intermediate Similarity	NPD5330	Approved
0.7353	Intermediate Similarity	NPD7521	Approved
0.7353	Intermediate Similarity	NPD7334	Approved
0.7353	Intermediate Similarity	NPD6409	Approved
0.7353	Intermediate Similarity	NPD7146	Approved
0.7345	Intermediate Similarity	NPD6899	Approved
0.7345	Intermediate Similarity	NPD7320	Approved
0.7345	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7328	Intermediate Similarity	NPD4632	Approved
0.7317	Intermediate Similarity	NPD7078	Approved
0.7315	Intermediate Similarity	NPD7902	Approved
0.7304	Intermediate Similarity	NPD8130	Phase 1
0.73	Intermediate Similarity	NPD3667	Approved
0.7288	Intermediate Similarity	NPD7115	Discovery
0.7281	Intermediate Similarity	NPD6373	Approved
0.7281	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD5701	Approved
0.7257	Intermediate Similarity	NPD5697	Approved
0.725	Intermediate Similarity	NPD6319	Approved
0.7248	Intermediate Similarity	NPD5696	Approved
0.7232	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7102	Approved
0.7217	Intermediate Similarity	NPD6883	Approved
0.7217	Intermediate Similarity	NPD7290	Approved
0.7213	Intermediate Similarity	NPD6067	Discontinued
0.7212	Intermediate Similarity	NPD6903	Approved
0.719	Intermediate Similarity	NPD6016	Approved
0.719	Intermediate Similarity	NPD6015	Approved
0.7184	Intermediate Similarity	NPD5279	Phase 3
0.717	Intermediate Similarity	NPD7515	Phase 2
0.717	Intermediate Similarity	NPD5284	Approved
0.717	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD5281	Approved
0.7157	Intermediate Similarity	NPD3666	Approved
0.7157	Intermediate Similarity	NPD3133	Approved
0.7157	Intermediate Similarity	NPD3665	Phase 1
0.7155	Intermediate Similarity	NPD6650	Approved
0.7155	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD6869	Approved
0.7155	Intermediate Similarity	NPD6649	Approved
0.7155	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD5328	Approved
0.7131	Intermediate Similarity	NPD5988	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.7091	Intermediate Similarity	NPD7638	Approved
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8513	Phase 3
0.7049	Intermediate Similarity	NPD8517	Approved
0.7049	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD8516	Approved
0.7043	Intermediate Similarity	NPD6011	Approved
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7640	Approved
0.7027	Intermediate Similarity	NPD7639	Approved
0.7019	Intermediate Similarity	NPD6098	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6050	Approved
0.7009	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD4755	Approved
0.6981	Remote Similarity	NPD6904	Approved
0.6981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6101	Approved
0.6981	Remote Similarity	NPD6080	Approved
0.6981	Remote Similarity	NPD6673	Approved
0.6944	Remote Similarity	NPD4202	Approved
0.6935	Remote Similarity	NPD7604	Phase 2
0.6916	Remote Similarity	NPD5692	Phase 3
0.6911	Remote Similarity	NPD5983	Phase 2
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.687	Remote Similarity	NPD6008	Approved
0.6852	Remote Similarity	NPD5694	Approved
0.685	Remote Similarity	NPD8336	Approved
0.685	Remote Similarity	NPD8337	Approved
0.685	Remote Similarity	NPD6033	Approved
0.6838	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3668	Phase 3
0.6825	Remote Similarity	NPD6336	Discontinued
0.6818	Remote Similarity	NPD5210	Approved
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4629	Approved
0.6807	Remote Similarity	NPD6053	Discontinued
0.6796	Remote Similarity	NPD4221	Approved
0.6796	Remote Similarity	NPD4223	Phase 3
0.6796	Remote Similarity	NPD6435	Approved
0.678	Remote Similarity	NPD4634	Approved
0.6777	Remote Similarity	NPD6274	Approved
0.6762	Remote Similarity	NPD5329	Approved
0.6759	Remote Similarity	NPD46	Approved
0.6759	Remote Similarity	NPD5207	Approved
0.6759	Remote Similarity	NPD6698	Approved
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5222	Approved
0.6757	Remote Similarity	NPD5221	Approved
0.6757	Remote Similarity	NPD4697	Phase 3
0.6754	Remote Similarity	NPD5224	Approved
0.6754	Remote Similarity	NPD5226	Approved
0.6754	Remote Similarity	NPD5211	Phase 2
0.6754	Remote Similarity	NPD5225	Approved
0.6754	Remote Similarity	NPD4633	Approved
0.6752	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7101	Approved
0.6748	Remote Similarity	NPD7100	Approved
0.6744	Remote Similarity	NPD5956	Approved
0.6733	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5208	Approved
0.6698	Remote Similarity	NPD4694	Approved
0.6698	Remote Similarity	NPD5280	Approved
0.6698	Remote Similarity	NPD5690	Phase 2
0.6697	Remote Similarity	NPD7637	Suspended
0.6697	Remote Similarity	NPD5693	Phase 1
0.6696	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD7122	Discontinued
0.664	Remote Similarity	NPD6908	Approved
0.664	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD6940	Discontinued
0.6638	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD8171	Discontinued
0.6636	Remote Similarity	NPD7524	Approved
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6602	Remote Similarity	NPD5368	Approved
0.6602	Remote Similarity	NPD7525	Registered
0.66	Remote Similarity	NPD6942	Approved
0.66	Remote Similarity	NPD7339	Approved
0.6585	Remote Similarity	NPD6317	Approved
0.6581	Remote Similarity	NPD4767	Approved
0.6581	Remote Similarity	NPD4768	Approved
0.6571	Remote Similarity	NPD4788	Approved
0.6552	Remote Similarity	NPD4754	Approved
0.6545	Remote Similarity	NPD7983	Approved
0.6542	Remote Similarity	NPD4693	Phase 3
0.6542	Remote Similarity	NPD4689	Approved
0.6542	Remote Similarity	NPD5205	Approved
0.6542	Remote Similarity	NPD4690	Approved
0.6542	Remote Similarity	NPD4138	Approved
0.6542	Remote Similarity	NPD4688	Approved
0.6538	Remote Similarity	NPD4139	Approved
0.6538	Remote Similarity	NPD4692	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