NPASS Compound

Structure

CID65829 OpenBabel06191715402D 32 32 0 0 1 0 0 0 0 0999 V2000 -4.9086 1.5804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1783 0.4023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1029 3.7344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7001 -1.2269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1368 -0.4007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8262 -0.5633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6235 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9757 -1.4311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5984 0.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0747 -0.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2786 1.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5232 -0.1083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1828 2.3802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1828 2.3802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2034 0.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0338 3.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4010 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4010 1.7568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6235 0.7818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8019 -0.8678 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.5483 0.1143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7029 -1.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1137 2.0149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8156 3.9926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7272 0.1294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8681 -0.6188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 3.1906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7776 -2.2989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2535 1.0698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 25 1 0 0 0 0 12 32 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 0 0 0 0 17 27 2 0 0 0 0 18 23 1 0 0 0 0 19 14 1 6 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 1 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 22 29 2 0 0 0 0 22 32 1 0 0 0 0 23 30 2 0 0 0 0 24 31 1 0 0 0 0 25 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.26
Volume:	478.112
LogP:	2.0
LogD:	1.035
LogS:	-3.138
# Rotatable Bonds:	11
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	4.807
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.651
MDCK Permeability:	2.7805390345747583e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.918
Plasma Protein Binding (PPB):	73.74381256103516%
Volume Distribution (VD):	1.082
Pgp-substrate:	13.252004623413086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.302
CYP3A4-substrate:	0.419

ADMET: Excretion

Clearance (CL):	4.038
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.298
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.962
Carcinogencity:	0.342
Eye Corrosion:	0.004
Eye Irritation:	0.042
Respiratory Toxicity:	0.804

Download Data

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

Natural Product: NPC65829

Natural Product ID:	NPC65829
*Common Name:**	Vibsanin W
IUPAC Name:	[(E)-2-[(1S,2S,7S)-2-(3,4-dihydroxy-4-methylpentyl)-5-(hydroxymethyl)-2-methyl-6-oxo-7-(2-oxopropyl)cyclohept-4-en-1-yl]ethenyl] 3-methylbut-2-enoate
Synonyms:	Vibsanin W
Standard InCHIKey:	QITBJTPHBLIQAN-SGVLUOOISA-N
Standard InCHI:	InChI=1S/C25H38O7/c1-16(2)13-22(29)32-12-9-20-19(14-17(3)27)23(30)18(15-26)7-10-25(20,6)11-8-21(28)24(4,5)31/h7,9,12-13,19-21,26,28,31H,8,10-11,14-15H2,1-6H3/b12-9+/t19-,20-,21?,25+/m0/s1
SMILES:	OCC1=CC[C@]([C@H]([C@@H](C1=O)CC(=O)C)/C=C/OC(=O)C=C(C)C)(C)CCC(C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516103
PubChem CID:	10411484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.18	ug ml-1	PMID[527256]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.6	ug ml-1	PMID[527256]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	8.15	ug ml-1	PMID[527256]

☑ 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 NPC65829 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	1188
0.2-0.3	4485
0.3-0.4	9364
0.4-0.5	14916
0.5-0.6	7591
0.6-0.7	4273
0.7-0.8	639
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC145666
0.8876	High Similarity	NPC478145
0.8876	High Similarity	NPC478144
0.8444	Intermediate Similarity	NPC11804
0.8444	Intermediate Similarity	NPC261380
0.8247	Intermediate Similarity	NPC53844
0.8222	Intermediate Similarity	NPC161045
0.8191	Intermediate Similarity	NPC473448
0.8155	Intermediate Similarity	NPC47951
0.8125	Intermediate Similarity	NPC167219
0.8111	Intermediate Similarity	NPC474291
0.8111	Intermediate Similarity	NPC85772
0.8043	Intermediate Similarity	NPC137033
0.8021	Intermediate Similarity	NPC469645
0.8021	Intermediate Similarity	NPC469692
0.798	Intermediate Similarity	NPC141191
0.798	Intermediate Similarity	NPC316598
0.7959	Intermediate Similarity	NPC185553
0.7957	Intermediate Similarity	NPC261721
0.7938	Intermediate Similarity	NPC121825
0.7925	Intermediate Similarity	NPC138757
0.7925	Intermediate Similarity	NPC76550
0.7925	Intermediate Similarity	NPC123855
0.7905	Intermediate Similarity	NPC257240
0.79	Intermediate Similarity	NPC54705
0.7879	Intermediate Similarity	NPC169205
0.7865	Intermediate Similarity	NPC192006
0.785	Intermediate Similarity	NPC46269
0.785	Intermediate Similarity	NPC106395
0.7849	Intermediate Similarity	NPC125290
0.7843	Intermediate Similarity	NPC472755
0.7843	Intermediate Similarity	NPC110989
0.7826	Intermediate Similarity	NPC11620
0.7822	Intermediate Similarity	NPC472753
0.7812	Intermediate Similarity	NPC51486
0.7812	Intermediate Similarity	NPC77337
0.781	Intermediate Similarity	NPC137911
0.781	Intermediate Similarity	NPC228477
0.7802	Intermediate Similarity	NPC325031
0.7789	Intermediate Similarity	NPC474471
0.7789	Intermediate Similarity	NPC227379
0.7789	Intermediate Similarity	NPC153805
0.7778	Intermediate Similarity	NPC138303
0.7778	Intermediate Similarity	NPC67290
0.7778	Intermediate Similarity	NPC133677
0.7767	Intermediate Similarity	NPC309190
0.7767	Intermediate Similarity	NPC203659
0.7766	Intermediate Similarity	NPC164393
0.7766	Intermediate Similarity	NPC315395
0.7766	Intermediate Similarity	NPC316426
0.7755	Intermediate Similarity	NPC469632
0.7755	Intermediate Similarity	NPC53685
0.7745	Intermediate Similarity	NPC225353
0.7745	Intermediate Similarity	NPC472754
0.7742	Intermediate Similarity	NPC70424
0.7742	Intermediate Similarity	NPC9868
0.7742	Intermediate Similarity	NPC243618
0.7736	Intermediate Similarity	NPC29133
0.7732	Intermediate Similarity	NPC261607
0.7732	Intermediate Similarity	NPC300312
0.7732	Intermediate Similarity	NPC475972
0.7732	Intermediate Similarity	NPC303697
0.7732	Intermediate Similarity	NPC111114
0.7732	Intermediate Similarity	NPC177037
0.7732	Intermediate Similarity	NPC472814
0.7727	Intermediate Similarity	NPC244166
0.7708	Intermediate Similarity	NPC212598
0.7708	Intermediate Similarity	NPC477215
0.7708	Intermediate Similarity	NPC476388
0.77	Intermediate Similarity	NPC477949
0.77	Intermediate Similarity	NPC40812
0.7692	Intermediate Similarity	NPC179891
0.7692	Intermediate Similarity	NPC475661
0.7692	Intermediate Similarity	NPC473488
0.7684	Intermediate Similarity	NPC248602
0.7677	Intermediate Similarity	NPC193645
0.7677	Intermediate Similarity	NPC90121
0.7677	Intermediate Similarity	NPC209355
0.7677	Intermediate Similarity	NPC275960
0.7677	Intermediate Similarity	NPC272050
0.7677	Intermediate Similarity	NPC48803
0.7677	Intermediate Similarity	NPC476488
0.7677	Intermediate Similarity	NPC476487
0.767	Intermediate Similarity	NPC475945
0.767	Intermediate Similarity	NPC475871
0.7667	Intermediate Similarity	NPC279532
0.7664	Intermediate Similarity	NPC324683
0.7664	Intermediate Similarity	NPC470961
0.766	Intermediate Similarity	NPC165162
0.7653	Intermediate Similarity	NPC115021
0.7647	Intermediate Similarity	NPC206079
0.7647	Intermediate Similarity	NPC128733
0.7647	Intermediate Similarity	NPC185141
0.7647	Intermediate Similarity	NPC46998
0.7647	Intermediate Similarity	NPC133907
0.7647	Intermediate Similarity	NPC474742
0.7647	Intermediate Similarity	NPC110443
0.7642	Intermediate Similarity	NPC477102
0.7634	Intermediate Similarity	NPC16488
0.7629	Intermediate Similarity	NPC476004
0.7629	Intermediate Similarity	NPC474761
0.7624	Intermediate Similarity	NPC83895
0.7624	Intermediate Similarity	NPC187761
0.7619	Intermediate Similarity	NPC329048
0.7619	Intermediate Similarity	NPC330011
0.7619	Intermediate Similarity	NPC473911
0.7609	Intermediate Similarity	NPC112868
0.7609	Intermediate Similarity	NPC474980
0.7604	Intermediate Similarity	NPC60765
0.7604	Intermediate Similarity	NPC476803
0.76	Intermediate Similarity	NPC473291
0.76	Intermediate Similarity	NPC242848
0.76	Intermediate Similarity	NPC9812
0.7596	Intermediate Similarity	NPC472756
0.7596	Intermediate Similarity	NPC100487
0.7593	Intermediate Similarity	NPC191620
0.7579	Intermediate Similarity	NPC472009
0.7579	Intermediate Similarity	NPC469483
0.7576	Intermediate Similarity	NPC477241
0.7576	Intermediate Similarity	NPC476415
0.7573	Intermediate Similarity	NPC474747
0.757	Intermediate Similarity	NPC477103
0.7553	Intermediate Similarity	NPC474776
0.7551	Intermediate Similarity	NPC476705
0.7551	Intermediate Similarity	NPC219874
0.7551	Intermediate Similarity	NPC284185
0.7547	Intermediate Similarity	NPC308191
0.7526	Intermediate Similarity	NPC268298
0.7526	Intermediate Similarity	NPC83423
0.7526	Intermediate Similarity	NPC5509
0.7525	Intermediate Similarity	NPC475709
0.7525	Intermediate Similarity	NPC253826
0.7525	Intermediate Similarity	NPC239895
0.75	Intermediate Similarity	NPC475873
0.75	Intermediate Similarity	NPC291154
0.75	Intermediate Similarity	NPC475050
0.75	Intermediate Similarity	NPC474490
0.75	Intermediate Similarity	NPC304886
0.75	Intermediate Similarity	NPC472007
0.75	Intermediate Similarity	NPC72513
0.75	Intermediate Similarity	NPC474765
0.75	Intermediate Similarity	NPC472469
0.75	Intermediate Similarity	NPC312561
0.7477	Intermediate Similarity	NPC475065
0.7476	Intermediate Similarity	NPC116139
0.7476	Intermediate Similarity	NPC477950
0.7476	Intermediate Similarity	NPC282524
0.7476	Intermediate Similarity	NPC150923
0.7475	Intermediate Similarity	NPC476416
0.7475	Intermediate Similarity	NPC476049
0.7474	Intermediate Similarity	NPC33570
0.7474	Intermediate Similarity	NPC21471
0.7473	Intermediate Similarity	NPC476627
0.7473	Intermediate Similarity	NPC128276
0.7455	Intermediate Similarity	NPC147912
0.7455	Intermediate Similarity	NPC67259
0.7453	Intermediate Similarity	NPC91034
0.7453	Intermediate Similarity	NPC473284
0.7451	Intermediate Similarity	NPC255592
0.7451	Intermediate Similarity	NPC64742
0.7451	Intermediate Similarity	NPC57079
0.7451	Intermediate Similarity	NPC261377
0.7451	Intermediate Similarity	NPC108368
0.7451	Intermediate Similarity	NPC161855
0.7451	Intermediate Similarity	NPC308567
0.7451	Intermediate Similarity	NPC244411
0.7449	Intermediate Similarity	NPC166554
0.7449	Intermediate Similarity	NPC265856
0.7449	Intermediate Similarity	NPC469368
0.7449	Intermediate Similarity	NPC476437
0.7449	Intermediate Similarity	NPC129419
0.7449	Intermediate Similarity	NPC232426
0.7449	Intermediate Similarity	NPC476369
0.7449	Intermediate Similarity	NPC253144
0.7449	Intermediate Similarity	NPC281942
0.7447	Intermediate Similarity	NPC477784
0.7447	Intermediate Similarity	NPC477786
0.7447	Intermediate Similarity	NPC23748
0.7447	Intermediate Similarity	NPC477785
0.7444	Intermediate Similarity	NPC203277
0.7444	Intermediate Similarity	NPC279537
0.7429	Intermediate Similarity	NPC220964
0.7429	Intermediate Similarity	NPC118911
0.7429	Intermediate Similarity	NPC121099
0.7429	Intermediate Similarity	NPC474741
0.7429	Intermediate Similarity	NPC475676
0.7426	Intermediate Similarity	NPC93271
0.7426	Intermediate Similarity	NPC184065
0.7426	Intermediate Similarity	NPC135576
0.7426	Intermediate Similarity	NPC202833
0.7423	Intermediate Similarity	NPC476805
0.7423	Intermediate Similarity	NPC104560
0.7423	Intermediate Similarity	NPC281516
0.7423	Intermediate Similarity	NPC472008
0.7419	Intermediate Similarity	NPC470241
0.7419	Intermediate Similarity	NPC471325
0.7419	Intermediate Similarity	NPC47031
0.7419	Intermediate Similarity	NPC40228
0.7419	Intermediate Similarity	NPC42470
0.7407	Intermediate Similarity	NPC37116

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 NPC65829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1767
0.2-0.3	3579
0.3-0.4	2312
0.4-0.5	886
0.5-0.6	326
0.6-0.7	64
0.7-0.8	9
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
0.8191	Intermediate Similarity	NPD5785	Approved
0.7905	Intermediate Similarity	NPD6371	Approved
0.7677	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5363	Approved
0.7473	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5786	Approved
0.734	Intermediate Similarity	NPD4270	Approved
0.734	Intermediate Similarity	NPD4269	Approved
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7282	Intermediate Similarity	NPD4225	Approved
0.7263	Intermediate Similarity	NPD7154	Phase 3
0.7234	Intermediate Similarity	NPD5369	Approved
0.7158	Intermediate Similarity	NPD5209	Approved
0.713	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4252	Approved
0.71	Intermediate Similarity	NPD46	Approved
0.71	Intermediate Similarity	NPD6698	Approved
0.7083	Intermediate Similarity	NPD5362	Discontinued
0.703	Intermediate Similarity	NPD7983	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6939	Remote Similarity	NPD1694	Approved
0.6931	Remote Similarity	NPD7838	Discovery
0.6909	Remote Similarity	NPD6686	Approved
0.6893	Remote Similarity	NPD5282	Discontinued
0.6863	Remote Similarity	NPD6411	Approved
0.6804	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4819	Approved
0.6771	Remote Similarity	NPD4821	Approved
0.6771	Remote Similarity	NPD4820	Approved
0.6771	Remote Similarity	NPD4822	Approved
0.6729	Remote Similarity	NPD7639	Approved
0.6729	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD7638	Approved
0.6633	Remote Similarity	NPD6435	Approved
0.6632	Remote Similarity	NPD4756	Discovery
0.6598	Remote Similarity	NPD5368	Approved
0.6598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD8039	Approved
0.6571	Remote Similarity	NPD7748	Approved
0.6566	Remote Similarity	NPD6110	Phase 1
0.6566	Remote Similarity	NPD5332	Approved
0.6566	Remote Similarity	NPD5331	Approved
0.6562	Remote Similarity	NPD4271	Approved
0.6562	Remote Similarity	NPD4268	Approved
0.6542	Remote Similarity	NPD6083	Phase 2
0.6542	Remote Similarity	NPD6084	Phase 2
0.6542	Remote Similarity	NPD7902	Approved
0.6538	Remote Similarity	NPD7637	Suspended
0.6531	Remote Similarity	NPD4790	Discontinued
0.6522	Remote Similarity	NPD6053	Discontinued
0.6505	Remote Similarity	NPD5370	Suspended
0.6476	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD4251	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD6899	Approved
0.6449	Remote Similarity	NPD7839	Suspended
0.6436	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD4695	Discontinued
0.6404	Remote Similarity	NPD3197	Phase 1
0.6381	Remote Similarity	NPD6079	Approved
0.6381	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8297	Approved
0.6373	Remote Similarity	NPD7146	Approved
0.6373	Remote Similarity	NPD5330	Approved
0.6373	Remote Similarity	NPD7521	Approved
0.6373	Remote Similarity	NPD4249	Approved
0.6373	Remote Similarity	NPD6684	Approved
0.6373	Remote Similarity	NPD4519	Discontinued
0.6373	Remote Similarity	NPD7334	Approved
0.6373	Remote Similarity	NPD4623	Approved
0.6373	Remote Similarity	NPD6409	Approved
0.6372	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD5695	Phase 3
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.6348	Remote Similarity	NPD7290	Approved
0.6337	Remote Similarity	NPD3133	Approved
0.6337	Remote Similarity	NPD3666	Approved
0.6337	Remote Similarity	NPD3665	Phase 1
0.6337	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD6011	Approved
0.6316	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5211	Phase 2
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8130	Phase 1
0.6293	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD5739	Approved
0.6283	Remote Similarity	NPD6675	Approved
0.6283	Remote Similarity	NPD7128	Approved
0.6283	Remote Similarity	NPD6402	Approved
0.6281	Remote Similarity	NPD6319	Approved
0.6273	Remote Similarity	NPD6648	Approved
0.6264	Remote Similarity	NPD7331	Phase 2
0.6262	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7900	Approved
0.6261	Remote Similarity	NPD6013	Approved
0.6261	Remote Similarity	NPD6372	Approved
0.6261	Remote Similarity	NPD6012	Approved
0.6261	Remote Similarity	NPD6014	Approved
0.6261	Remote Similarity	NPD6373	Approved
0.6261	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6672	Approved
0.625	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6226	Remote Similarity	NPD5693	Phase 1
0.6226	Remote Similarity	NPD5284	Approved
0.6226	Remote Similarity	NPD5281	Approved
0.6214	Remote Similarity	NPD5279	Phase 3
0.6214	Remote Similarity	NPD3618	Phase 1
0.6214	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4634	Approved
0.6204	Remote Similarity	NPD5210	Approved
0.6204	Remote Similarity	NPD4629	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.619	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4753	Phase 2
0.619	Remote Similarity	NPD5328	Approved
0.619	Remote Similarity	NPD1695	Approved
0.6182	Remote Similarity	NPD5696	Approved
0.6176	Remote Similarity	NPD4786	Approved
0.6174	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD7341	Phase 2
0.6147	Remote Similarity	NPD5222	Approved
0.6147	Remote Similarity	NPD5221	Approved
0.6147	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD7319	Approved
0.6139	Remote Similarity	NPD3667	Approved
0.6126	Remote Similarity	NPD4696	Approved
0.6126	Remote Similarity	NPD5285	Approved
0.6126	Remote Similarity	NPD5286	Approved
0.6117	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6647	Phase 2
0.61	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8517	Approved
0.6098	Remote Similarity	NPD8513	Phase 3
0.6098	Remote Similarity	NPD8515	Approved
0.6098	Remote Similarity	NPD7503	Approved
0.6098	Remote Similarity	NPD8516	Approved
0.6091	Remote Similarity	NPD5173	Approved
0.6087	Remote Similarity	NPD6412	Phase 2
0.6087	Remote Similarity	NPD5701	Approved
0.608	Remote Similarity	NPD7492	Approved
0.6078	Remote Similarity	NPD4788	Approved
0.6071	Remote Similarity	NPD5223	Approved
0.6068	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5690	Phase 2
0.6038	Remote Similarity	NPD6904	Approved
0.6038	Remote Similarity	NPD6080	Approved
0.6038	Remote Similarity	NPD6673	Approved
0.6033	Remote Similarity	NPD6009	Approved
0.6033	Remote Similarity	NPD7500	Approved
0.6032	Remote Similarity	NPD6616	Approved
0.6032	Remote Similarity	NPD7507	Approved
0.6032	Remote Similarity	NPD8273	Phase 1
0.6019	Remote Similarity	NPD4202	Approved
0.6018	Remote Similarity	NPD5225	Approved
0.6018	Remote Similarity	NPD5226	Approved
0.6018	Remote Similarity	NPD5224	Approved
0.6018	Remote Similarity	NPD4633	Approved
0.6017	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD7642	Approved
0.5984	Remote Similarity	NPD6335	Approved
0.5984	Remote Similarity	NPD7078	Approved
0.5983	Remote Similarity	NPD6413	Approved
0.598	Remote Similarity	NPD4223	Phase 3
0.598	Remote Similarity	NPD4221	Approved
0.5965	Remote Similarity	NPD5175	Approved
0.5965	Remote Similarity	NPD5174	Approved
0.5962	Remote Similarity	NPD5329	Approved
0.5962	Remote Similarity	NPD1696	Phase 3
0.595	Remote Similarity	NPD6868	Approved
0.5946	Remote Similarity	NPD4755	Approved
0.594	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7736	Approved
0.5935	Remote Similarity	NPD7100	Approved
0.5935	Remote Similarity	NPD7101	Approved
0.5926	Remote Similarity	NPD5694	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