NPASS Compound

Structure

NPC475802 OpenBabel07101718182D 36 39 0 0 1 0 0 0 0 0999 V2000 3.2720 -2.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 -5.8097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1891 -4.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1371 1.7814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0129 -0.2457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0036 -1.8280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7749 1.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7717 -3.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -3.6427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3447 -2.5526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3447 -1.5776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3447 -1.5776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3447 -2.5526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2594 -5.0209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3447 -4.5026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8325 1.6795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0829 -3.3414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5004 -3.0401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7717 -0.7888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6560 -1.5776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0829 -0.7888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7717 0.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5004 -1.0901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6560 -2.5526 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7102 -5.1228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3447 -5.4776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4056 2.4683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0729 1.7161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9879 -0.2457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6560 -4.1302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5004 -4.0151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2291 0.7888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3447 -0.0000 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 18 1 0 0 0 0 11 23 1 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 24 1 6 0 0 0 17 32 1 0 0 0 0 18 24 1 1 0 0 0 18 33 1 0 0 0 0 19 26 1 1 0 0 0 19 35 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 6 0 0 0 20 24 1 0 0 0 0 21 26 1 6 0 0 0 21 34 1 0 0 0 0 22 25 1 0 0 0 0 22 30 2 0 0 0 0 22 35 1 0 0 0 0 23 5 1 6 0 0 0 23 31 1 0 0 0 0 24 6 1 6 0 0 0 25 26 1 6 0 0 0 25 36 1 0 0 0 0 26 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.22
Volume:	496.11
LogP:	1.916
LogD:	1.223
LogS:	-4.262
# Rotatable Bonds:	6
TPSA:	137.96
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	6.08
Fsp3:	0.692
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:	-5.11
MDCK Permeability:	0.00010103709064424038
Pgp-inhibitor:	1.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.524
20% Bioavailability (F20%):	0.248
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.703
Plasma Protein Binding (PPB):	47.74892044067383%
Volume Distribution (VD):	1.585
Pgp-substrate:	48.20232391357422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.216
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	2.852
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.413
Rat Oral Acute Toxicity:	0.914
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.428
Carcinogencity:	0.296
Eye Corrosion:	0.026
Eye Irritation:	0.022
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC475802

Natural Product ID:	NPC475802
*Common Name:**	SYJNBQCZPKCZCU-HMOXNCNNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SYJNBQCZPKCZCU-HMOXNCNNSA-N
Standard InCHI:	InChI=1S/C26H34O10/c1-13-8-9-17(32-14(2)27)24(6)18(33-15(3)28)10-11-23(5,31)20(24)21(34-16(4)29)26-19(12-13)35-22(30)25(26,7)36-26/h10-12,17-21,31H,8-9H2,1-7H3/b13-12-/t17-,18-,19-,20-,21-,23+,24-,25-,26+/m0/s1
SMILES:	CC(=O)O[C@H]1CC/C(=C[C@H]2[C@]3([C@H]([C@@H]4[C@]1(C)[C@H](C=C[C@@]4(C)O)OC(=O)C)OC(=O)C)O[C@@]3(C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516396
PubChem CID:	44575458
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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[460959]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460959]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460959]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[460959]

☑ 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 NPC475802 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	215
0.1-0.2	1303
0.2-0.3	4614
0.3-0.4	9120
0.4-0.5	13931
0.5-0.6	7798
0.6-0.7	4545
0.7-0.8	1032
0.8-0.85	89
0.85-0.9	27
0.9-0.95	5
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC474664
0.9798	High Similarity	NPC14862
0.9798	High Similarity	NPC233379
0.9796	High Similarity	NPC16313
0.9796	High Similarity	NPC9303
0.97	High Similarity	NPC15218
0.9697	High Similarity	NPC326994
0.9697	High Similarity	NPC324327
0.9697	High Similarity	NPC194620
0.9697	High Similarity	NPC72813
0.9697	High Similarity	NPC474421
0.96	High Similarity	NPC169888
0.96	High Similarity	NPC55972
0.96	High Similarity	NPC327286
0.9495	High Similarity	NPC220964
0.9495	High Similarity	NPC475676
0.9412	High Similarity	NPC115257
0.9412	High Similarity	NPC161816
0.9394	High Similarity	NPC4620
0.9314	High Similarity	NPC475922
0.92	High Similarity	NPC19239
0.92	High Similarity	NPC474166
0.8911	High Similarity	NPC183571
0.8868	High Similarity	NPC473877
0.8824	High Similarity	NPC69171
0.8824	High Similarity	NPC474165
0.875	High Similarity	NPC475510
0.875	High Similarity	NPC475587
0.8679	High Similarity	NPC281624
0.8667	High Similarity	NPC94377
0.8667	High Similarity	NPC473939
0.8667	High Similarity	NPC473595
0.8627	High Similarity	NPC474339
0.8627	High Similarity	NPC164598
0.8624	High Similarity	NPC474333
0.8585	High Similarity	NPC42662
0.8545	High Similarity	NPC296822
0.8544	High Similarity	NPC471148
0.8519	High Similarity	NPC317687
0.8515	High Similarity	NPC471140
0.8505	High Similarity	NPC473843
0.8505	High Similarity	NPC473975
0.8505	High Similarity	NPC473594
0.8505	High Similarity	NPC474586
0.8426	Intermediate Similarity	NPC317107
0.8426	Intermediate Similarity	NPC194619
0.8416	Intermediate Similarity	NPC230800
0.8416	Intermediate Similarity	NPC279621
0.8396	Intermediate Similarity	NPC477513
0.8381	Intermediate Similarity	NPC472756
0.8365	Intermediate Similarity	NPC472754
0.8365	Intermediate Similarity	NPC149371
0.8364	Intermediate Similarity	NPC73314
0.835	Intermediate Similarity	NPC288876
0.835	Intermediate Similarity	NPC475949
0.8318	Intermediate Similarity	NPC322903
0.8317	Intermediate Similarity	NPC475659
0.8288	Intermediate Similarity	NPC476710
0.8288	Intermediate Similarity	NPC476711
0.8286	Intermediate Similarity	NPC472755
0.8269	Intermediate Similarity	NPC264477
0.8269	Intermediate Similarity	NPC472753
0.8269	Intermediate Similarity	NPC47880
0.8269	Intermediate Similarity	NPC477511
0.8235	Intermediate Similarity	NPC473859
0.8235	Intermediate Similarity	NPC17585
0.8235	Intermediate Similarity	NPC476315
0.8218	Intermediate Similarity	NPC474247
0.8214	Intermediate Similarity	NPC476713
0.8214	Intermediate Similarity	NPC476712
0.8214	Intermediate Similarity	NPC471146
0.8208	Intermediate Similarity	NPC474741
0.8208	Intermediate Similarity	NPC471143
0.8208	Intermediate Similarity	NPC477510
0.8182	Intermediate Similarity	NPC475971
0.8173	Intermediate Similarity	NPC477512
0.8131	Intermediate Similarity	NPC472751
0.8131	Intermediate Similarity	NPC472749
0.8125	Intermediate Similarity	NPC270478
0.8119	Intermediate Similarity	NPC228451
0.8119	Intermediate Similarity	NPC125674
0.8119	Intermediate Similarity	NPC475838
0.8095	Intermediate Similarity	NPC201718
0.8077	Intermediate Similarity	NPC471144
0.807	Intermediate Similarity	NPC470186
0.8039	Intermediate Similarity	NPC303942
0.8039	Intermediate Similarity	NPC57405
0.8037	Intermediate Similarity	NPC146731
0.8037	Intermediate Similarity	NPC258532
0.8037	Intermediate Similarity	NPC472748
0.8019	Intermediate Similarity	NPC105725
0.8	Intermediate Similarity	NPC5103
0.7982	Intermediate Similarity	NPC474286
0.7982	Intermediate Similarity	NPC475130
0.798	Intermediate Similarity	NPC266957
0.7963	Intermediate Similarity	NPC314244
0.7961	Intermediate Similarity	NPC270013
0.7961	Intermediate Similarity	NPC14961
0.7961	Intermediate Similarity	NPC471142
0.7961	Intermediate Similarity	NPC36954
0.7961	Intermediate Similarity	NPC471141
0.7946	Intermediate Similarity	NPC469463
0.7946	Intermediate Similarity	NPC469496
0.7946	Intermediate Similarity	NPC477126
0.7946	Intermediate Similarity	NPC469454
0.7944	Intermediate Similarity	NPC475945
0.7944	Intermediate Similarity	NPC472747
0.7944	Intermediate Similarity	NPC472750
0.7944	Intermediate Similarity	NPC475871
0.7941	Intermediate Similarity	NPC476300
0.7928	Intermediate Similarity	NPC304180
0.7928	Intermediate Similarity	NPC179798
0.7925	Intermediate Similarity	NPC474742
0.7921	Intermediate Similarity	NPC144133
0.7921	Intermediate Similarity	NPC475748
0.7921	Intermediate Similarity	NPC475855
0.7921	Intermediate Similarity	NPC179394
0.7921	Intermediate Similarity	NPC469368
0.7913	Intermediate Similarity	NPC477092
0.7905	Intermediate Similarity	NPC222303
0.79	Intermediate Similarity	NPC287089
0.7895	Intermediate Similarity	NPC469684
0.7895	Intermediate Similarity	NPC471145
0.7895	Intermediate Similarity	NPC475305
0.789	Intermediate Similarity	NPC26617
0.7879	Intermediate Similarity	NPC50637
0.7879	Intermediate Similarity	NPC478112
0.787	Intermediate Similarity	NPC296950
0.7864	Intermediate Similarity	NPC81386
0.7864	Intermediate Similarity	NPC471147
0.7864	Intermediate Similarity	NPC474035
0.7863	Intermediate Similarity	NPC310035
0.7863	Intermediate Similarity	NPC188222
0.7863	Intermediate Similarity	NPC282003
0.785	Intermediate Similarity	NPC474747
0.785	Intermediate Similarity	NPC49393
0.7845	Intermediate Similarity	NPC475003
0.7843	Intermediate Similarity	NPC20713
0.7826	Intermediate Similarity	NPC475401
0.7822	Intermediate Similarity	NPC151770
0.7818	Intermediate Similarity	NPC117604
0.7818	Intermediate Similarity	NPC308191
0.781	Intermediate Similarity	NPC40812
0.7807	Intermediate Similarity	NPC477509
0.7798	Intermediate Similarity	NPC179891
0.7798	Intermediate Similarity	NPC123726
0.7798	Intermediate Similarity	NPC284365
0.7797	Intermediate Similarity	NPC303006
0.7797	Intermediate Similarity	NPC67251
0.7788	Intermediate Similarity	NPC159333
0.7788	Intermediate Similarity	NPC107476
0.7788	Intermediate Similarity	NPC56448
0.7778	Intermediate Similarity	NPC475321
0.7768	Intermediate Similarity	NPC287311
0.7768	Intermediate Similarity	NPC475495
0.7767	Intermediate Similarity	NPC475912
0.7767	Intermediate Similarity	NPC212486
0.7757	Intermediate Similarity	NPC15993
0.7757	Intermediate Similarity	NPC207885
0.7757	Intermediate Similarity	NPC476270
0.7748	Intermediate Similarity	NPC477102
0.7745	Intermediate Similarity	NPC474232
0.7745	Intermediate Similarity	NPC51004
0.7739	Intermediate Similarity	NPC23046
0.7739	Intermediate Similarity	NPC473590
0.7736	Intermediate Similarity	NPC470188
0.7736	Intermediate Similarity	NPC255592
0.7736	Intermediate Similarity	NPC473326
0.7736	Intermediate Similarity	NPC161855
0.7736	Intermediate Similarity	NPC208233
0.7736	Intermediate Similarity	NPC308567
0.7736	Intermediate Similarity	NPC261377
0.7727	Intermediate Similarity	NPC266514
0.7723	Intermediate Similarity	NPC476803
0.7723	Intermediate Similarity	NPC476805
0.7714	Intermediate Similarity	NPC39859
0.7714	Intermediate Similarity	NPC54731
0.7714	Intermediate Similarity	NPC158416
0.7714	Intermediate Similarity	NPC470883
0.7714	Intermediate Similarity	NPC76862
0.7712	Intermediate Similarity	NPC23786
0.7712	Intermediate Similarity	NPC470265
0.7706	Intermediate Similarity	NPC203659
0.77	Intermediate Similarity	NPC278283
0.7699	Intermediate Similarity	NPC473522
0.7699	Intermediate Similarity	NPC269530
0.7699	Intermediate Similarity	NPC475277
0.7699	Intermediate Similarity	NPC477093
0.7699	Intermediate Similarity	NPC66108
0.7692	Intermediate Similarity	NPC473316
0.7692	Intermediate Similarity	NPC121825
0.7692	Intermediate Similarity	NPC476267
0.7692	Intermediate Similarity	NPC140543
0.7692	Intermediate Similarity	NPC473330
0.7685	Intermediate Similarity	NPC324017
0.7685	Intermediate Similarity	NPC471757
0.7685	Intermediate Similarity	NPC473596
0.7685	Intermediate Similarity	NPC78127
0.7685	Intermediate Similarity	NPC39996
0.7685	Intermediate Similarity	NPC320019

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 NPC475802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1796
0.2-0.3	3705
0.3-0.4	2293
0.4-0.5	731
0.5-0.6	313
0.6-0.7	113
0.7-0.8	11
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
0.789	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6698	Approved
0.7745	Intermediate Similarity	NPD46	Approved
0.7679	Intermediate Similarity	NPD6371	Approved
0.7611	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5282	Discontinued
0.75	Intermediate Similarity	NPD7983	Approved
0.7426	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7115	Discovery
0.7264	Intermediate Similarity	NPD5779	Approved
0.7264	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD7838	Discovery
0.719	Intermediate Similarity	NPD8517	Approved
0.719	Intermediate Similarity	NPD8513	Phase 3
0.719	Intermediate Similarity	NPD8515	Approved
0.719	Intermediate Similarity	NPD8516	Approved
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD5785	Approved
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6686	Approved
0.6981	Remote Similarity	NPD1695	Approved
0.6964	Remote Similarity	NPD5344	Discontinued
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8074	Phase 3
0.6897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6648	Approved
0.6852	Remote Similarity	NPD6411	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.6838	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6319	Approved
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4270	Approved
0.6796	Remote Similarity	NPD4269	Approved
0.6792	Remote Similarity	NPD4251	Approved
0.6792	Remote Similarity	NPD4250	Approved
0.6757	Remote Similarity	NPD7839	Suspended
0.6746	Remote Similarity	NPD7492	Approved
0.6731	Remote Similarity	NPD7154	Phase 3
0.6699	Remote Similarity	NPD5369	Approved
0.6698	Remote Similarity	NPD5786	Approved
0.6698	Remote Similarity	NPD4249	Approved
0.6694	Remote Similarity	NPD6054	Approved
0.6693	Remote Similarity	NPD8273	Phase 1
0.6693	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6641	Remote Similarity	NPD7078	Approved
0.6636	Remote Similarity	NPD6399	Phase 3
0.6604	Remote Similarity	NPD5363	Approved
0.6604	Remote Similarity	NPD1694	Approved
0.6602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4821	Approved
0.6602	Remote Similarity	NPD4252	Approved
0.6602	Remote Similarity	NPD4822	Approved
0.6602	Remote Similarity	NPD4819	Approved
0.6602	Remote Similarity	NPD4820	Approved
0.6589	Remote Similarity	NPD7736	Approved
0.6587	Remote Similarity	NPD6370	Approved
0.6585	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6650	Approved
0.6583	Remote Similarity	NPD6649	Approved
0.6579	Remote Similarity	NPD7639	Approved
0.6579	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD5362	Discontinued
0.6569	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7260	Phase 2
0.656	Remote Similarity	NPD6059	Approved
0.6555	Remote Similarity	NPD6373	Approved
0.6555	Remote Similarity	NPD6372	Approved
0.6549	Remote Similarity	NPD6083	Phase 2
0.6549	Remote Similarity	NPD6084	Phase 2
0.6535	Remote Similarity	NPD8328	Phase 3
0.6529	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD5695	Phase 3
0.6512	Remote Similarity	NPD8293	Discontinued
0.6508	Remote Similarity	NPD6015	Approved
0.6508	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD5696	Approved
0.6491	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6457	Remote Similarity	NPD5988	Approved
0.6441	Remote Similarity	NPD5739	Approved
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6441	Remote Similarity	NPD6008	Approved
0.6436	Remote Similarity	NPD8039	Approved
0.6415	Remote Similarity	NPD6110	Phase 1
0.6412	Remote Similarity	NPD7319	Approved
0.6408	Remote Similarity	NPD4271	Approved
0.6408	Remote Similarity	NPD4268	Approved
0.6406	Remote Similarity	NPD7604	Phase 2
0.6406	Remote Similarity	NPD7642	Approved
0.6393	Remote Similarity	NPD6882	Approved
0.6387	Remote Similarity	NPD5697	Approved
0.6378	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD7290	Approved
0.6364	Remote Similarity	NPD6883	Approved
0.6341	Remote Similarity	NPD4632	Approved
0.6333	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD6435	Approved
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5209	Approved
0.632	Remote Similarity	NPD6009	Approved
0.6311	Remote Similarity	NPD6617	Approved
0.6311	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD6847	Approved
0.6311	Remote Similarity	NPD6869	Approved
0.6308	Remote Similarity	NPD7507	Approved
0.6308	Remote Similarity	NPD8451	Approved
0.6296	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6013	Approved
0.6281	Remote Similarity	NPD6014	Approved
0.6281	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD7829	Approved
0.6279	Remote Similarity	NPD7830	Approved
0.6273	Remote Similarity	NPD6672	Approved
0.6273	Remote Similarity	NPD5737	Approved
0.6269	Remote Similarity	NPD6845	Suspended
0.626	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD5983	Phase 2
0.6231	Remote Similarity	NPD8299	Approved
0.6231	Remote Similarity	NPD8341	Approved
0.6231	Remote Similarity	NPD8342	Approved
0.6231	Remote Similarity	NPD8340	Approved
0.621	Remote Similarity	NPD8133	Approved
0.6204	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD7500	Approved
0.6183	Remote Similarity	NPD6336	Discontinued
0.6182	Remote Similarity	NPD7524	Approved
0.6179	Remote Similarity	NPD2204	Approved
0.6174	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5368	Approved
0.6124	Remote Similarity	NPD7503	Approved
0.6124	Remote Similarity	NPD8444	Approved
0.6121	Remote Similarity	NPD7902	Approved
0.6119	Remote Similarity	NPD5956	Approved
0.6119	Remote Similarity	NPD8390	Approved
0.6119	Remote Similarity	NPD8392	Approved
0.6119	Remote Similarity	NPD8391	Approved
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD6695	Phase 3
0.6111	Remote Similarity	NPD5331	Approved
0.6106	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD1700	Approved
0.6098	Remote Similarity	NPD4634	Approved
0.6098	Remote Similarity	NPD6421	Discontinued
0.6091	Remote Similarity	NPD6098	Approved
0.609	Remote Similarity	NPD6033	Approved
0.6075	Remote Similarity	NPD4790	Discontinued
0.6071	Remote Similarity	NPD6080	Approved
0.6071	Remote Similarity	NPD5370	Suspended
0.6071	Remote Similarity	NPD6904	Approved
0.6071	Remote Similarity	NPD6673	Approved
0.605	Remote Similarity	NPD7632	Discontinued
0.605	Remote Similarity	NPD5211	Phase 2
0.6048	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7328	Approved
0.6016	Remote Similarity	NPD7327	Approved
0.6014	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4756	Discovery
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8033	Approved
0.5969	Remote Similarity	NPD7101	Approved
0.5969	Remote Similarity	NPD7100	Approved
0.5969	Remote Similarity	NPD7516	Approved
0.5965	Remote Similarity	NPD5281	Approved
0.5965	Remote Similarity	NPD6050	Approved
0.5965	Remote Similarity	NPD5694	Approved
0.5965	Remote Similarity	NPD5284	Approved
0.5954	Remote Similarity	NPD8080	Discontinued
0.595	Remote Similarity	NPD5141	Approved
0.5948	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD5210	Approved
0.5948	Remote Similarity	NPD4629	Approved
0.5946	Remote Similarity	NPD7521	Approved
0.5946	Remote Similarity	NPD7334	Approved
0.5946	Remote Similarity	NPD5330	Approved
0.5946	Remote Similarity	NPD6684	Approved
0.5946	Remote Similarity	NPD7146	Approved
0.5946	Remote Similarity	NPD6409	Approved
0.5942	Remote Similarity	NPD8415	Approved
0.5929	Remote Similarity	NPD4753	Phase 2
0.5929	Remote Similarity	NPD6051	Approved
0.5923	Remote Similarity	NPD8294	Approved
0.5923	Remote Similarity	NPD8377	Approved
0.5909	Remote Similarity	NPD4786	Approved
0.5893	Remote Similarity	NPD7750	Discontinued

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