NPASS Compound

Structure

CID145666 OpenBabel06191715502D 31 31 0 0 1 0 0 0 0 0999 V2000 3.7368 -3.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3919 -3.0431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5051 3.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8593 2.1965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5276 -3.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9888 0.1490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8019 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2581 1.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 -1.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3653 0.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4922 -2.1530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1222 -1.8650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0329 -2.6577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9994 -1.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4170 -2.8206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8705 2.3455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5304 -3.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0245 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4010 -1.7568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2225 -0.9749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2470 1.5637 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.1473 -1.6425 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6796 -0.4644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0965 -4.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6123 0.6328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8525 -0.6869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8349 -2.6577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4671 -2.3755 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 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 7 10 1 0 0 0 0 7 19 2 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 25 1 0 0 0 0 12 31 1 0 0 0 0 13 16 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 17 22 1 0 0 0 0 18 27 2 0 0 0 0 19 24 1 0 0 0 0 20 14 1 1 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 1 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 30 2 0 0 0 0 25 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	466.686
LogP:	2.173
LogD:	0.336
LogS:	-2.059
# Rotatable Bonds:	12
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.175
Synthetic Accessibility Score:	5.076
Fsp3:	0.6
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:	2.136544389941264e-05
Pgp-inhibitor:	0.256
Pgp-substrate:	0.743
Human Intestinal Absorption (HIA):	0.321
20% Bioavailability (F20%):	0.415
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.738
Plasma Protein Binding (PPB):	55.43456268310547%
Volume Distribution (VD):	0.835
Pgp-substrate:	40.421504974365234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.164
CYP2C9-substrate:	0.253
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.884
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	5.989
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.757
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.793
Skin Sensitization:	0.919
Carcinogencity:	0.054
Eye Corrosion:	0.658
Eye Irritation:	0.095
Respiratory Toxicity:	0.47

Download Data

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

Natural Product: NPC145666

Natural Product ID:	NPC145666
*Common Name:**	5-Epi-Vibsanin G
IUPAC Name:	[(E)-2-[(1S,2S,7R)-5-(hydroxymethyl)-2-(3-hydroxy-4-methylpent-4-enyl)-2-methyl-6-oxo-7-(2-oxopropyl)cyclohept-4-en-1-yl]ethenyl] 3-methylbut-2-enoate
Synonyms:	5-Epi-Vibsanin G
Standard InCHIKey:	HOUIWALHPPJDOP-CZRULFJLSA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-16(2)13-23(29)31-12-9-21-20(14-18(5)27)24(30)19(15-26)7-10-25(21,6)11-8-22(28)17(3)4/h7,9,12-13,20-22,26,28H,3,8,10-11,14-15H2,1-2,4-6H3/b12-9+/t20-,21+,22?,25-/m1/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(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480093
PubChem CID:	10388101
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
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141874]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	leaves and flowers	n.a.	n.a.	PMID[14738390]
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]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO18814	Viburnum odoratissimum	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2477	Cell Line	NUGC-3	Homo sapiens	Survival	=	58.0	%	PMID[473725]

☑ 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 NPC145666 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	212
0.1-0.2	1155
0.2-0.3	4575
0.3-0.4	10157
0.4-0.5	14591
0.5-0.6	7122
0.6-0.7	4126
0.7-0.8	740
0.8-0.85	13
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC65829
0.9186	High Similarity	NPC478144
0.8966	High Similarity	NPC478145
0.8523	High Similarity	NPC261380
0.8511	High Similarity	NPC53844
0.8229	Intermediate Similarity	NPC141191
0.8222	Intermediate Similarity	NPC261721
0.8211	Intermediate Similarity	NPC185553
0.8191	Intermediate Similarity	NPC167219
0.8182	Intermediate Similarity	NPC85772
0.814	Intermediate Similarity	NPC192006
0.8125	Intermediate Similarity	NPC169205
0.8111	Intermediate Similarity	NPC11804
0.8065	Intermediate Similarity	NPC51486
0.8041	Intermediate Similarity	NPC316598
0.8022	Intermediate Similarity	NPC315395
0.8022	Intermediate Similarity	NPC316426
0.8	Intermediate Similarity	NPC244166
0.8	Intermediate Similarity	NPC53685
0.7979	Intermediate Similarity	NPC472814
0.7979	Intermediate Similarity	NPC177037
0.7959	Intermediate Similarity	NPC54705
0.7917	Intermediate Similarity	NPC48803
0.7917	Intermediate Similarity	NPC476487
0.7917	Intermediate Similarity	NPC275960
0.7917	Intermediate Similarity	NPC90121
0.7917	Intermediate Similarity	NPC476488
0.7917	Intermediate Similarity	NPC193645
0.7917	Intermediate Similarity	NPC209355
0.7912	Intermediate Similarity	NPC125290
0.7912	Intermediate Similarity	NPC165162
0.7895	Intermediate Similarity	NPC469645
0.7895	Intermediate Similarity	NPC469692
0.7895	Intermediate Similarity	NPC115021
0.7889	Intermediate Similarity	NPC16488
0.7889	Intermediate Similarity	NPC161045
0.7872	Intermediate Similarity	NPC77337
0.7872	Intermediate Similarity	NPC473448
0.7865	Intermediate Similarity	NPC325031
0.7864	Intermediate Similarity	NPC47951
0.7864	Intermediate Similarity	NPC228477
0.7864	Intermediate Similarity	NPC137911
0.7835	Intermediate Similarity	NPC242848
0.7822	Intermediate Similarity	NPC309190
0.7812	Intermediate Similarity	NPC469632
0.7812	Intermediate Similarity	NPC121825
0.7789	Intermediate Similarity	NPC219874
0.7789	Intermediate Similarity	NPC261607
0.7789	Intermediate Similarity	NPC284185
0.7789	Intermediate Similarity	NPC300312
0.7789	Intermediate Similarity	NPC111114
0.7778	Intermediate Similarity	NPC474291
0.7766	Intermediate Similarity	NPC268298
0.7766	Intermediate Similarity	NPC212598
0.7766	Intermediate Similarity	NPC5509
0.7755	Intermediate Similarity	NPC477949
0.7755	Intermediate Similarity	NPC475709
0.7755	Intermediate Similarity	NPC253826
0.7742	Intermediate Similarity	NPC312561
0.7727	Intermediate Similarity	NPC128276
0.7723	Intermediate Similarity	NPC110989
0.7717	Intermediate Similarity	NPC33570
0.7717	Intermediate Similarity	NPC137033
0.7717	Intermediate Similarity	NPC21471
0.7701	Intermediate Similarity	NPC279537
0.77	Intermediate Similarity	NPC206079
0.7684	Intermediate Similarity	NPC253144
0.7684	Intermediate Similarity	NPC232426
0.7684	Intermediate Similarity	NPC469368
0.7684	Intermediate Similarity	NPC281942
0.7684	Intermediate Similarity	NPC129419
0.7677	Intermediate Similarity	NPC108368
0.7677	Intermediate Similarity	NPC57079
0.767	Intermediate Similarity	NPC91034
0.7667	Intermediate Similarity	NPC470241
0.7667	Intermediate Similarity	NPC471325
0.7667	Intermediate Similarity	NPC42470
0.7667	Intermediate Similarity	NPC40228
0.7667	Intermediate Similarity	NPC47031
0.7667	Intermediate Similarity	NPC112868
0.766	Intermediate Similarity	NPC474471
0.766	Intermediate Similarity	NPC476805
0.766	Intermediate Similarity	NPC104560
0.766	Intermediate Similarity	NPC60765
0.766	Intermediate Similarity	NPC227379
0.7653	Intermediate Similarity	NPC9812
0.7653	Intermediate Similarity	NPC184065
0.7653	Intermediate Similarity	NPC202833
0.7647	Intermediate Similarity	NPC203659
0.7642	Intermediate Similarity	NPC76550
0.7642	Intermediate Similarity	NPC123855
0.7642	Intermediate Similarity	NPC138757
0.764	Intermediate Similarity	NPC470244
0.764	Intermediate Similarity	NPC470239
0.7634	Intermediate Similarity	NPC469483
0.7634	Intermediate Similarity	NPC305475
0.7634	Intermediate Similarity	NPC194417
0.7634	Intermediate Similarity	NPC475461
0.7629	Intermediate Similarity	NPC476415
0.7624	Intermediate Similarity	NPC225353
0.7619	Intermediate Similarity	NPC257240
0.7614	Intermediate Similarity	NPC57744
0.7609	Intermediate Similarity	NPC31086
0.7604	Intermediate Similarity	NPC150978
0.7604	Intermediate Similarity	NPC74103
0.7604	Intermediate Similarity	NPC141831
0.7604	Intermediate Similarity	NPC123177
0.7604	Intermediate Similarity	NPC70595
0.76	Intermediate Similarity	NPC469872
0.76	Intermediate Similarity	NPC469864
0.7596	Intermediate Similarity	NPC220155
0.7582	Intermediate Similarity	NPC7414
0.7582	Intermediate Similarity	NPC471296
0.7582	Intermediate Similarity	NPC89555
0.7579	Intermediate Similarity	NPC477215
0.7579	Intermediate Similarity	NPC476388
0.7579	Intermediate Similarity	NPC174342
0.7579	Intermediate Similarity	NPC117405
0.7579	Intermediate Similarity	NPC52198
0.7576	Intermediate Similarity	NPC208094
0.7576	Intermediate Similarity	NPC202705
0.7576	Intermediate Similarity	NPC474343
0.7573	Intermediate Similarity	NPC266570
0.7573	Intermediate Similarity	NPC189863
0.757	Intermediate Similarity	NPC106395
0.757	Intermediate Similarity	NPC46269
0.7558	Intermediate Similarity	NPC275098
0.7556	Intermediate Similarity	NPC306095
0.7553	Intermediate Similarity	NPC237540
0.7553	Intermediate Similarity	NPC72513
0.7551	Intermediate Similarity	NPC304886
0.7551	Intermediate Similarity	NPC474490
0.7549	Intermediate Similarity	NPC472755
0.7549	Intermediate Similarity	NPC476889
0.7549	Intermediate Similarity	NPC291154
0.7528	Intermediate Similarity	NPC476627
0.7528	Intermediate Similarity	NPC315765
0.7528	Intermediate Similarity	NPC108816
0.7528	Intermediate Similarity	NPC297996
0.7528	Intermediate Similarity	NPC93763
0.7528	Intermediate Similarity	NPC475994
0.7527	Intermediate Similarity	NPC65661
0.7527	Intermediate Similarity	NPC86316
0.7527	Intermediate Similarity	NPC106416
0.7527	Intermediate Similarity	NPC255307
0.7527	Intermediate Similarity	NPC470755
0.7526	Intermediate Similarity	NPC476049
0.7526	Intermediate Similarity	NPC139692
0.7526	Intermediate Similarity	NPC476416
0.7525	Intermediate Similarity	NPC477950
0.7525	Intermediate Similarity	NPC244456
0.7525	Intermediate Similarity	NPC469657
0.7525	Intermediate Similarity	NPC116139
0.7525	Intermediate Similarity	NPC472753
0.7525	Intermediate Similarity	NPC282524
0.75	Intermediate Similarity	NPC67290
0.75	Intermediate Similarity	NPC318468
0.75	Intermediate Similarity	NPC11620
0.75	Intermediate Similarity	NPC16279
0.75	Intermediate Similarity	NPC476369
0.75	Intermediate Similarity	NPC256640
0.75	Intermediate Similarity	NPC138303
0.75	Intermediate Similarity	NPC476437
0.75	Intermediate Similarity	NPC477147
0.75	Intermediate Similarity	NPC244411
0.75	Intermediate Similarity	NPC205615
0.75	Intermediate Similarity	NPC133677
0.75	Intermediate Similarity	NPC64742
0.75	Intermediate Similarity	NPC477149
0.75	Intermediate Similarity	NPC473455
0.7476	Intermediate Similarity	NPC118911
0.7475	Intermediate Similarity	NPC29152
0.7475	Intermediate Similarity	NPC473291
0.7475	Intermediate Similarity	NPC476797
0.7475	Intermediate Similarity	NPC134072
0.7475	Intermediate Similarity	NPC234993
0.7475	Intermediate Similarity	NPC301534
0.7475	Intermediate Similarity	NPC250757
0.7474	Intermediate Similarity	NPC53454
0.7474	Intermediate Similarity	NPC153805
0.7474	Intermediate Similarity	NPC143025
0.7474	Intermediate Similarity	NPC476803
0.7474	Intermediate Similarity	NPC475819
0.7473	Intermediate Similarity	NPC25684
0.7473	Intermediate Similarity	NPC474980
0.7473	Intermediate Similarity	NPC301477
0.7473	Intermediate Similarity	NPC281949
0.7473	Intermediate Similarity	NPC229584
0.7473	Intermediate Similarity	NPC14203
0.7453	Intermediate Similarity	NPC29133
0.7451	Intermediate Similarity	NPC40918
0.7451	Intermediate Similarity	NPC66110
0.7451	Intermediate Similarity	NPC472754
0.7451	Intermediate Similarity	NPC476890
0.7451	Intermediate Similarity	NPC478156
0.7449	Intermediate Similarity	NPC470697
0.7449	Intermediate Similarity	NPC148463
0.7449	Intermediate Similarity	NPC475572
0.7447	Intermediate Similarity	NPC474045
0.7447	Intermediate Similarity	NPC202394

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 NPC145666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1737
0.2-0.3	3573
0.3-0.4	2381
0.4-0.5	857
0.5-0.6	316
0.6-0.7	79
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD5785	Approved
0.7917	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD5363	Approved
0.7727	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5786	Approved
0.7619	Intermediate Similarity	NPD6371	Approved
0.7582	Intermediate Similarity	NPD4270	Approved
0.7582	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD7154	Phase 3
0.7391	Intermediate Similarity	NPD5209	Approved
0.7363	Intermediate Similarity	NPD4252	Approved
0.7312	Intermediate Similarity	NPD5362	Discontinued
0.7283	Intermediate Similarity	NPD5369	Approved
0.7204	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.7158	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD6411	Approved
0.7054	Intermediate Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD7515	Phase 2
0.69	Remote Similarity	NPD7983	Approved
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6101	Approved
0.6852	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4756	Discovery
0.6842	Remote Similarity	NPD6435	Approved
0.6827	Remote Similarity	NPD7638	Approved
0.6813	Remote Similarity	NPD8039	Approved
0.6809	Remote Similarity	NPD4819	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6809	Remote Similarity	NPD4820	Approved
0.6809	Remote Similarity	NPD4821	Approved
0.6809	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4822	Approved
0.68	Remote Similarity	NPD7838	Discovery
0.6789	Remote Similarity	NPD6686	Approved
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD4268	Approved
0.6771	Remote Similarity	NPD5331	Approved
0.6771	Remote Similarity	NPD5332	Approved
0.6765	Remote Similarity	NPD7748	Approved
0.6737	Remote Similarity	NPD4790	Discontinued
0.6733	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD7902	Approved
0.67	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7839	Suspended
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4695	Discontinued
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6079	Approved
0.6566	Remote Similarity	NPD7146	Approved
0.6566	Remote Similarity	NPD6409	Approved
0.6566	Remote Similarity	NPD4249	Approved
0.6566	Remote Similarity	NPD7334	Approved
0.6566	Remote Similarity	NPD6684	Approved
0.6566	Remote Similarity	NPD5330	Approved
0.6566	Remote Similarity	NPD7521	Approved
0.6549	Remote Similarity	NPD6053	Discontinued
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3666	Approved
0.6531	Remote Similarity	NPD3133	Approved
0.6531	Remote Similarity	NPD3665	Phase 1
0.6495	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6899	Approved
0.6486	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6649	Approved
0.6442	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD6903	Approved
0.6436	Remote Similarity	NPD6672	Approved
0.6436	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6110	Phase 1
0.64	Remote Similarity	NPD4519	Discontinued
0.64	Remote Similarity	NPD3618	Phase 1
0.64	Remote Similarity	NPD5279	Phase 3
0.64	Remote Similarity	NPD4623	Approved
0.6396	Remote Similarity	NPD5697	Approved
0.6389	Remote Similarity	NPD5344	Discontinued
0.6381	Remote Similarity	NPD5695	Phase 3
0.6373	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5328	Approved
0.6372	Remote Similarity	NPD7290	Approved
0.6372	Remote Similarity	NPD6883	Approved
0.6372	Remote Similarity	NPD7102	Approved
0.6364	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4786	Approved
0.6339	Remote Similarity	NPD6011	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.633	Remote Similarity	NPD5211	Phase 2
0.6327	Remote Similarity	NPD3667	Approved
0.6321	Remote Similarity	NPD5221	Approved
0.6321	Remote Similarity	NPD5222	Approved
0.6321	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8130	Phase 1
0.6316	Remote Similarity	NPD6847	Approved
0.6316	Remote Similarity	NPD6869	Approved
0.6316	Remote Similarity	NPD6617	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.6306	Remote Similarity	NPD5739	Approved
0.6292	Remote Similarity	NPD7331	Phase 2
0.6289	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6372	Approved
0.6283	Remote Similarity	NPD6013	Approved
0.6283	Remote Similarity	NPD6373	Approved
0.6283	Remote Similarity	NPD6014	Approved
0.6283	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6647	Phase 2
0.6262	Remote Similarity	NPD5173	Approved
0.6261	Remote Similarity	NPD8297	Approved
0.6261	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD3197	Phase 1
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD5284	Approved
0.6238	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6214	Remote Similarity	NPD1695	Approved
0.6214	Remote Similarity	NPD4753	Phase 2
0.6204	Remote Similarity	NPD5696	Approved
0.6195	Remote Similarity	NPD7320	Approved
0.618	Remote Similarity	NPD7341	Phase 2
0.6176	Remote Similarity	NPD3573	Approved
0.6174	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4697	Phase 3
0.6147	Remote Similarity	NPD5286	Approved
0.6147	Remote Similarity	NPD6648	Approved
0.6147	Remote Similarity	NPD4696	Approved
0.6147	Remote Similarity	NPD5285	Approved
0.614	Remote Similarity	NPD6413	Approved
0.6111	Remote Similarity	NPD3704	Approved
0.6111	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5701	Approved
0.6102	Remote Similarity	NPD6868	Approved
0.61	Remote Similarity	NPD4788	Approved
0.6091	Remote Similarity	NPD5223	Approved
0.6082	Remote Similarity	NPD3732	Approved
0.6078	Remote Similarity	NPD5690	Phase 2
0.6068	Remote Similarity	NPD4632	Approved
0.6058	Remote Similarity	NPD6673	Approved
0.6058	Remote Similarity	NPD6080	Approved
0.6058	Remote Similarity	NPD6904	Approved
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7500	Approved
0.6044	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4202	Approved
0.6036	Remote Similarity	NPD5224	Approved
0.6036	Remote Similarity	NPD5226	Approved
0.6036	Remote Similarity	NPD4633	Approved
0.6036	Remote Similarity	NPD5225	Approved
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6319	Approved
0.6019	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6404	Discontinued
0.6	Remote Similarity	NPD4221	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD4223	Phase 3
0.5982	Remote Similarity	NPD5175	Approved
0.5982	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD5329	Approved
0.598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.598	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.598	Remote Similarity	NPD1696	Phase 3
0.5968	Remote Similarity	NPD7492	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5963	Remote Similarity	NPD4755	Approved
0.5955	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3194	Approved
0.5952	Remote Similarity	NPD3195	Phase 2
0.5952	Remote Similarity	NPD3196	Approved
0.5952	Remote Similarity	NPD4266	Approved
0.5952	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7100	Approved
0.595	Remote Similarity	NPD7101	Approved
0.5948	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD4634	Approved
0.5943	Remote Similarity	NPD6050	Approved
0.5943	Remote Similarity	NPD8034	Phase 2
0.5943	Remote Similarity	NPD8035	Phase 2
0.5943	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