NPASS Compound

Structure

CID316708 OpenBabel06191716132D 43 45 0 0 1 0 0 0 0 0999 V2000 -3.9937 -10.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9345 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7450 0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3765 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9937 -9.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9345 -2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1277 -8.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1277 -7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -7.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9345 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0540 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3546 1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2024 -0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9345 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0322 -0.5862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0238 2.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -4.0827 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 8 1 0 0 0 0 2 9 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 10 1 0 0 0 0 9 21 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 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 26 2 0 0 0 0 20 25 1 0 0 0 0 20 27 1 0 0 0 0 22 29 1 0 0 0 0 22 33 1 1 0 0 0 23 35 2 0 0 0 0 23 40 1 0 0 0 0 24 36 2 0 0 0 0 24 41 1 0 0 0 0 25 42 1 1 0 0 0 26 31 1 0 0 0 0 27 33 1 6 0 0 0 27 34 1 0 0 0 0 28 37 2 0 0 0 0 28 42 1 0 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 34 1 6 0 0 0 30 39 1 0 0 0 0 31 40 1 1 0 0 0 31 43 1 0 0 0 0 32 34 1 1 0 0 0 32 41 1 0 0 0 0 32 43 1 0 0 0 0 33 7 1 6 0 0 0 34 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.33
Volume:	628.971
LogP:	4.465
LogD:	2.625
LogS:	-4.411
# Rotatable Bonds:	15
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.077
Synthetic Accessibility Score:	5.999
Fsp3:	0.618
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:	-4.755
MDCK Permeability:	8.523927681380883e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	96.4201889038086%
Volume Distribution (VD):	2.494
Pgp-substrate:	3.2939095497131348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.359
CYP2C9-inhibitor:	0.449
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	2.43
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.553
Human Hepatotoxicity (H-HT):	0.788
Drug-inuced Liver Injury (DILI):	0.496
AMES Toxicity:	0.835
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.857
Carcinogencity:	0.609
Eye Corrosion:	0.017
Eye Irritation:	0.012
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC316708

Natural Product ID:	NPC316708
*Common Name:**	Argutin C
IUPAC Name:	[(1S,3R,5R,6aS,7S,8S,9R,10S,10aS)-1,3-diacetyloxy-9,10-dihydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] (2Z,4E)-deca-2,4-dienoate
Synonyms:	Argutin C
Standard InCHIKey:	SYVLIZAFBWNVCK-DEHQYFKSSA-N
Standard InCHI:	InChI=1S/C34H48O9/c1-8-10-11-12-13-14-15-16-28(37)42-25-19-26-31(40-23(5)35)43-32(41-24(6)36)34(26)27(20-25)33(7,18-17-21(3)9-2)22(4)29(38)30(34)39/h9,13-17,19,22,25,27,29-32,38-39H,2,8,10-12,18,20H2,1,3-7H3/b14-13+,16-15-,21-17+/t22-,25+,27+,29-,30-,31+,32-,33-,34-/m1/s1
SMILES:	CCCCCC=CC=CC(=O)OC1CC2C(C(C(C(C23C(OC(C3=C1)OC(=O)C)OC(=O)C)O)O)C)(C)CC=C(C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651114
PubChem CID:	53323549
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21067210]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21067210]
NPO22840	Casearia arguta	Species	Salicaceae	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
EC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	1600.0	nM	PMID[489228]
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	3100.0	nM	PMID[489228]
NPT369	Cell Line	ACHN	Homo sapiens	Ratio EC50	=	1.9	n.a.	PMID[489228]

☑ 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 NPC316708 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	198
0.1-0.2	1182
0.2-0.3	3854
0.3-0.4	6887
0.4-0.5	13671
0.5-0.6	8568
0.6-0.7	5821
0.7-0.8	2349
0.8-0.85	76
0.85-0.9	39
0.9-0.95	38
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC470026
0.9806	High Similarity	NPC317460
0.9806	High Similarity	NPC328074
0.9806	High Similarity	NPC321272
0.9806	High Similarity	NPC470025
0.9712	High Similarity	NPC470027
0.9709	High Similarity	NPC17791
0.9703	High Similarity	NPC109376
0.9608	High Similarity	NPC470024
0.9608	High Similarity	NPC224660
0.9604	High Similarity	NPC172867
0.9417	High Similarity	NPC311223
0.9327	High Similarity	NPC316974
0.9327	High Similarity	NPC40728
0.932	High Similarity	NPC125423
0.932	High Similarity	NPC88013
0.9238	High Similarity	NPC119550
0.9231	High Similarity	NPC217921
0.9231	High Similarity	NPC128795
0.9231	High Similarity	NPC135015
0.9231	High Similarity	NPC48548
0.9223	High Similarity	NPC218158
0.9126	High Similarity	NPC473207
0.9126	High Similarity	NPC264867
0.9126	High Similarity	NPC470321
0.9126	High Similarity	NPC201880
0.9126	High Similarity	NPC81567
0.9029	High Similarity	NPC127933
0.9029	High Similarity	NPC134270
0.9029	High Similarity	NPC475889
0.9029	High Similarity	NPC7644
0.9029	High Similarity	NPC7613
0.8952	High Similarity	NPC184512
0.8932	High Similarity	NPC471363
0.8932	High Similarity	NPC238397
0.8857	High Similarity	NPC252296
0.8812	High Similarity	NPC171598
0.875	High Similarity	NPC470914
0.8738	High Similarity	NPC473545
0.8738	High Similarity	NPC473204
0.8738	High Similarity	NPC472187
0.8725	High Similarity	NPC98112
0.8713	High Similarity	NPC471362
0.8713	High Similarity	NPC471372
0.8713	High Similarity	NPC472189
0.8704	High Similarity	NPC177047
0.8679	High Similarity	NPC82251
0.8641	High Similarity	NPC318917
0.8641	High Similarity	NPC471366
0.8641	High Similarity	NPC472186
0.8641	High Similarity	NPC476800
0.8611	High Similarity	NPC206618
0.8571	High Similarity	NPC11956
0.8544	High Similarity	NPC472188
0.8522	High Similarity	NPC471082
0.8519	High Similarity	NPC38948
0.8505	High Similarity	NPC239961
0.8496	Intermediate Similarity	NPC473617
0.8496	Intermediate Similarity	NPC473828
0.8491	Intermediate Similarity	NPC120009
0.8491	Intermediate Similarity	NPC281378
0.8491	Intermediate Similarity	NPC23584
0.8476	Intermediate Similarity	NPC472554
0.8476	Intermediate Similarity	NPC198992
0.8468	Intermediate Similarity	NPC264153
0.8468	Intermediate Similarity	NPC473159
0.8462	Intermediate Similarity	NPC474440
0.8426	Intermediate Similarity	NPC472390
0.8426	Intermediate Similarity	NPC475074
0.8411	Intermediate Similarity	NPC470768
0.8396	Intermediate Similarity	NPC472552
0.8381	Intermediate Similarity	NPC477968
0.8381	Intermediate Similarity	NPC219285
0.8381	Intermediate Similarity	NPC477971
0.8381	Intermediate Similarity	NPC477972
0.8381	Intermediate Similarity	NPC228251
0.8381	Intermediate Similarity	NPC20113
0.8381	Intermediate Similarity	NPC161527
0.8378	Intermediate Similarity	NPC473125
0.8349	Intermediate Similarity	NPC475263
0.8333	Intermediate Similarity	NPC470515
0.8333	Intermediate Similarity	NPC470767
0.8333	Intermediate Similarity	NPC470763
0.8319	Intermediate Similarity	NPC207637
0.8318	Intermediate Similarity	NPC45897
0.8318	Intermediate Similarity	NPC474124
0.8318	Intermediate Similarity	NPC474575
0.8304	Intermediate Similarity	NPC49413
0.8304	Intermediate Similarity	NPC290608
0.8304	Intermediate Similarity	NPC44298
0.8304	Intermediate Similarity	NPC473128
0.8304	Intermediate Similarity	NPC40133
0.8302	Intermediate Similarity	NPC280991
0.8286	Intermediate Similarity	NPC473154
0.8276	Intermediate Similarity	NPC170084
0.8276	Intermediate Similarity	NPC476204
0.8276	Intermediate Similarity	NPC233500
0.8261	Intermediate Similarity	NPC470915
0.8261	Intermediate Similarity	NPC219656
0.8261	Intermediate Similarity	NPC470911
0.8261	Intermediate Similarity	NPC470517
0.8257	Intermediate Similarity	NPC473586
0.8252	Intermediate Similarity	NPC88507
0.8252	Intermediate Similarity	NPC469491
0.8246	Intermediate Similarity	NPC473968
0.8246	Intermediate Similarity	NPC23046
0.8246	Intermediate Similarity	NPC203862
0.823	Intermediate Similarity	NPC475163
0.8224	Intermediate Similarity	NPC472815
0.8224	Intermediate Similarity	NPC470571
0.8224	Intermediate Similarity	NPC475344
0.8224	Intermediate Similarity	NPC150463
0.8224	Intermediate Similarity	NPC121423
0.8224	Intermediate Similarity	NPC476471
0.8224	Intermediate Similarity	NPC201191
0.8218	Intermediate Similarity	NPC470819
0.8214	Intermediate Similarity	NPC231797
0.8208	Intermediate Similarity	NPC324841
0.8205	Intermediate Similarity	NPC196130
0.819	Intermediate Similarity	NPC239547
0.819	Intermediate Similarity	NPC91197
0.819	Intermediate Similarity	NPC125551
0.819	Intermediate Similarity	NPC48692
0.819	Intermediate Similarity	NPC155319
0.819	Intermediate Similarity	NPC96597
0.819	Intermediate Similarity	NPC135369
0.819	Intermediate Similarity	NPC309503
0.8182	Intermediate Similarity	NPC50124
0.8173	Intermediate Similarity	NPC286612
0.8173	Intermediate Similarity	NPC230347
0.8173	Intermediate Similarity	NPC275310
0.8165	Intermediate Similarity	NPC51719
0.8165	Intermediate Similarity	NPC88349
0.8158	Intermediate Similarity	NPC471816
0.8151	Intermediate Similarity	NPC179261
0.8148	Intermediate Similarity	NPC473070
0.8142	Intermediate Similarity	NPC287075
0.8142	Intermediate Similarity	NPC157441
0.8137	Intermediate Similarity	NPC469403
0.8137	Intermediate Similarity	NPC470817
0.8136	Intermediate Similarity	NPC219804
0.8136	Intermediate Similarity	NPC41129
0.8131	Intermediate Similarity	NPC11974
0.8131	Intermediate Similarity	NPC475617
0.8125	Intermediate Similarity	NPC208189
0.8125	Intermediate Similarity	NPC65034
0.8113	Intermediate Similarity	NPC477928
0.8108	Intermediate Similarity	NPC257853
0.8108	Intermediate Similarity	NPC475586
0.8103	Intermediate Similarity	NPC122971
0.8103	Intermediate Similarity	NPC476529
0.8103	Intermediate Similarity	NPC5883
0.8103	Intermediate Similarity	NPC475775
0.8103	Intermediate Similarity	NPC153085
0.8103	Intermediate Similarity	NPC44899
0.8103	Intermediate Similarity	NPC268326
0.8103	Intermediate Similarity	NPC304260
0.8103	Intermediate Similarity	NPC29639
0.8099	Intermediate Similarity	NPC471407
0.8099	Intermediate Similarity	NPC476966
0.8095	Intermediate Similarity	NPC165632
0.8095	Intermediate Similarity	NPC8954
0.8095	Intermediate Similarity	NPC473153
0.8095	Intermediate Similarity	NPC94905
0.8095	Intermediate Similarity	NPC311166
0.8091	Intermediate Similarity	NPC33053
0.8091	Intermediate Similarity	NPC122816
0.8091	Intermediate Similarity	NPC471205
0.8091	Intermediate Similarity	NPC293512
0.8087	Intermediate Similarity	NPC152615
0.8087	Intermediate Similarity	NPC474483
0.8087	Intermediate Similarity	NPC93883
0.8077	Intermediate Similarity	NPC470255
0.8077	Intermediate Similarity	NPC256368
0.8073	Intermediate Similarity	NPC194941
0.8073	Intermediate Similarity	NPC85593
0.8073	Intermediate Similarity	NPC473543
0.8073	Intermediate Similarity	NPC473068
0.8073	Intermediate Similarity	NPC31430
0.8073	Intermediate Similarity	NPC93352
0.8067	Intermediate Similarity	NPC86346
0.8067	Intermediate Similarity	NPC469379
0.8067	Intermediate Similarity	NPC75856
0.8056	Intermediate Similarity	NPC273668
0.8056	Intermediate Similarity	NPC214277
0.8053	Intermediate Similarity	NPC194951
0.8053	Intermediate Similarity	NPC12046
0.8037	Intermediate Similarity	NPC64348
0.8037	Intermediate Similarity	NPC38855
0.8037	Intermediate Similarity	NPC188968
0.8037	Intermediate Similarity	NPC474190
0.8036	Intermediate Similarity	NPC191439
0.8036	Intermediate Similarity	NPC83005
0.8036	Intermediate Similarity	NPC235014
0.8036	Intermediate Similarity	NPC103627
0.8036	Intermediate Similarity	NPC170974
0.8034	Intermediate Similarity	NPC107338
0.8034	Intermediate Similarity	NPC257610
0.8034	Intermediate Similarity	NPC470312
0.8034	Intermediate Similarity	NPC109607

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 NPC316708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1335
0.2-0.3	3669
0.3-0.4	2564
0.4-0.5	921
0.5-0.6	305
0.6-0.7	165
0.7-0.8	24
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
0.8276	Intermediate Similarity	NPD7503	Approved
0.8018	Intermediate Similarity	NPD6686	Approved
0.7966	Intermediate Similarity	NPD8033	Approved
0.7949	Intermediate Similarity	NPD7516	Approved
0.7881	Intermediate Similarity	NPD8294	Approved
0.7881	Intermediate Similarity	NPD8377	Approved
0.7863	Intermediate Similarity	NPD7328	Approved
0.7863	Intermediate Similarity	NPD7327	Approved
0.7815	Intermediate Similarity	NPD8380	Approved
0.7815	Intermediate Similarity	NPD8379	Approved
0.7815	Intermediate Similarity	NPD8378	Approved
0.7815	Intermediate Similarity	NPD8296	Approved
0.7815	Intermediate Similarity	NPD8335	Approved
0.7636	Intermediate Similarity	NPD5344	Discontinued
0.7619	Intermediate Similarity	NPD7838	Discovery
0.7615	Intermediate Similarity	NPD4225	Approved
0.7545	Intermediate Similarity	NPD6648	Approved
0.7521	Intermediate Similarity	NPD8516	Approved
0.7521	Intermediate Similarity	NPD8517	Approved
0.7521	Intermediate Similarity	NPD8515	Approved
0.7521	Intermediate Similarity	NPD8513	Phase 3
0.7455	Intermediate Similarity	NPD7638	Approved
0.7455	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7507	Approved
0.7387	Intermediate Similarity	NPD7640	Approved
0.7387	Intermediate Similarity	NPD7639	Approved
0.7328	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7319	Approved
0.7212	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7736	Approved
0.7155	Intermediate Similarity	NPD6412	Phase 2
0.712	Intermediate Similarity	NPD8328	Phase 3
0.7083	Intermediate Similarity	NPD8133	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.704	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.6975	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD8074	Phase 3
0.6953	Remote Similarity	NPD8293	Discontinued
0.6929	Remote Similarity	NPD7492	Approved
0.6911	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6054	Approved
0.6875	Remote Similarity	NPD6616	Approved
0.686	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD7078	Approved
0.6818	Remote Similarity	NPD46	Approved
0.6818	Remote Similarity	NPD6698	Approved
0.681	Remote Similarity	NPD7632	Discontinued
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6009	Approved
0.6757	Remote Similarity	NPD7637	Suspended
0.6746	Remote Similarity	NPD6319	Approved
0.6723	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7524	Approved
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6693	Remote Similarity	NPD6015	Approved
0.6693	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6641	Remote Similarity	NPD5988	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6637	Remote Similarity	NPD7748	Approved
0.6614	Remote Similarity	NPD6059	Approved
0.6609	Remote Similarity	NPD7902	Approved
0.6607	Remote Similarity	NPD7983	Approved
0.6589	Remote Similarity	NPD6067	Discontinued
0.6589	Remote Similarity	NPD7829	Approved
0.6589	Remote Similarity	NPD7830	Approved
0.6583	Remote Similarity	NPD5697	Approved
0.6583	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7290	Approved
0.6557	Remote Similarity	NPD7102	Approved
0.6557	Remote Similarity	NPD6883	Approved
0.6529	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8264	Approved
0.6504	Remote Similarity	NPD6847	Approved
0.6504	Remote Similarity	NPD6617	Approved
0.6504	Remote Similarity	NPD6869	Approved
0.65	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7128	Approved
0.65	Remote Similarity	NPD6675	Approved
0.6493	Remote Similarity	NPD7260	Phase 2
0.6481	Remote Similarity	NPD6695	Phase 3
0.6475	Remote Similarity	NPD6372	Approved
0.6475	Remote Similarity	NPD6013	Approved
0.6475	Remote Similarity	NPD6373	Approved
0.6475	Remote Similarity	NPD6014	Approved
0.6475	Remote Similarity	NPD6012	Approved
0.646	Remote Similarity	NPD6411	Approved
0.646	Remote Similarity	NPD7515	Phase 2
0.6452	Remote Similarity	NPD6053	Discontinued
0.6434	Remote Similarity	NPD7625	Phase 1
0.6423	Remote Similarity	NPD6371	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6396	Remote Similarity	NPD7750	Discontinued
0.6393	Remote Similarity	NPD6011	Approved
0.6393	Remote Similarity	NPD7320	Approved
0.6389	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6008	Approved
0.6348	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7900	Approved
0.6336	Remote Similarity	NPD7604	Phase 2
0.6316	Remote Similarity	NPD6079	Approved
0.6311	Remote Similarity	NPD5701	Approved
0.6308	Remote Similarity	NPD5983	Phase 2
0.6293	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4634	Approved
0.6283	Remote Similarity	NPD6051	Approved
0.6283	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6101	Approved
0.6262	Remote Similarity	NPD6929	Approved
0.6262	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5211	Phase 2
0.6241	Remote Similarity	NPD8451	Approved
0.6241	Remote Similarity	NPD6336	Discontinued
0.6239	Remote Similarity	NPD7839	Suspended
0.6226	Remote Similarity	NPD7799	Discontinued
0.6218	Remote Similarity	NPD5286	Approved
0.6218	Remote Similarity	NPD4696	Approved
0.6218	Remote Similarity	NPD5285	Approved
0.6204	Remote Similarity	NPD7514	Phase 3
0.6204	Remote Similarity	NPD6930	Phase 2
0.6204	Remote Similarity	NPD7332	Phase 2
0.6204	Remote Similarity	NPD6845	Suspended
0.6204	Remote Similarity	NPD7525	Registered
0.6204	Remote Similarity	NPD6931	Approved
0.6202	Remote Similarity	NPD7641	Discontinued
0.6194	Remote Similarity	NPD8448	Approved
0.6188	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD6084	Phase 2
0.6183	Remote Similarity	NPD8444	Approved
0.6168	Remote Similarity	NPD7145	Approved
0.6161	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD6033	Approved
0.6148	Remote Similarity	NPD5141	Approved
0.6147	Remote Similarity	NPD6902	Approved
0.614	Remote Similarity	NPD5328	Approved
0.6136	Remote Similarity	NPD5126	Approved
0.6136	Remote Similarity	NPD5125	Phase 3
0.6132	Remote Similarity	NPD6933	Approved
0.6121	Remote Similarity	NPD8171	Discontinued
0.6116	Remote Similarity	NPD5224	Approved
0.6116	Remote Similarity	NPD5225	Approved
0.6116	Remote Similarity	NPD5226	Approved
0.6116	Remote Similarity	NPD4633	Approved
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7266	Discontinued
0.6106	Remote Similarity	NPD4251	Approved
0.6106	Remote Similarity	NPD4250	Approved
0.6102	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5222	Approved
0.6102	Remote Similarity	NPD5221	Approved
0.6087	Remote Similarity	NPD5785	Approved
0.6087	Remote Similarity	NPD8449	Approved
0.6087	Remote Similarity	NPD3168	Discontinued
0.6077	Remote Similarity	NPD6335	Approved
0.6075	Remote Similarity	NPD5776	Phase 2
0.6075	Remote Similarity	NPD6932	Approved
0.6075	Remote Similarity	NPD6925	Approved
0.6066	Remote Similarity	NPD5174	Approved
0.6066	Remote Similarity	NPD5175	Approved
0.6061	Remote Similarity	NPD6921	Approved
0.6058	Remote Similarity	NPD8391	Approved
0.6058	Remote Similarity	NPD8390	Approved
0.6058	Remote Similarity	NPD8392	Approved
0.6055	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5173	Approved
0.605	Remote Similarity	NPD4755	Approved
0.6047	Remote Similarity	NPD6274	Approved
0.6047	Remote Similarity	NPD6868	Approved
0.6045	Remote Similarity	NPD8341	Approved
0.6045	Remote Similarity	NPD8340	Approved
0.6045	Remote Similarity	NPD8342	Approved
0.6045	Remote Similarity	NPD8299	Approved
0.6043	Remote Similarity	NPD8450	Suspended
0.6038	Remote Similarity	NPD6942	Approved
0.6038	Remote Similarity	NPD8039	Approved
0.6038	Remote Similarity	NPD7339	Approved
0.6034	Remote Similarity	NPD5284	Approved
0.6034	Remote Similarity	NPD8034	Phase 2
0.6034	Remote Similarity	NPD7087	Discontinued
0.6034	Remote Similarity	NPD8035	Phase 2
0.6034	Remote Similarity	NPD5281	Approved
0.6033	Remote Similarity	NPD4159	Approved
0.6033	Remote Similarity	NPD5223	Approved
0.6018	Remote Similarity	NPD4249	Approved
0.6018	Remote Similarity	NPD7521	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