NPASS Compound

Structure

CID203277 OpenBabel06191715592D 31 31 0 0 1 0 0 0 0 0999 V2000 -2.5692 1.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2934 0.9059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8218 -5.4672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1317 -4.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2642 -3.8859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0476 0.9989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6547 -4.4494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3007 -2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9190 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7972 -1.7456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8905 -5.4212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6953 -4.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4595 -3.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3818 -2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9595 0.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2887 -0.5050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7060 -1.8879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3838 0.4905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7162 -1.7456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5738 -0.7557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6549 -0.7557 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3791 -0.9204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8500 -5.7029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4595 -3.1958 0.0000 C 0 0 2 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 4.0776 -2.8163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4835 -0.3403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2840 -1.9159 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0858 -6.6747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8888 0.4582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5645 -0.3403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 15 2 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 24 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 0 0 0 0 19 20 1 0 0 0 0 20 27 2 0 0 0 0 21 25 1 1 0 0 0 21 31 1 0 0 0 0 22 28 2 0 0 0 0 22 31 1 0 0 0 0 23 29 1 0 0 0 0 24 5 1 1 0 0 0 25 6 1 1 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.25
Volume:	466.686
LogP:	2.399
LogD:	1.827
LogS:	-3.953
# Rotatable Bonds:	7
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.527
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.651
MDCK Permeability:	1.2001909453829285e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.149
Human Intestinal Absorption (HIA):	0.198
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912
Plasma Protein Binding (PPB):	79.71617889404297%
Volume Distribution (VD):	0.496
Pgp-substrate:	12.857641220092773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.301
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.833
CYP2D6-inhibitor:	0.285
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	1.8
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.693
Carcinogencity:	0.246
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC203277

Natural Product ID:	NPC203277
*Common Name:**	Vabsanol A
IUPAC Name:	[(1R,2E,4S,6Z,9E,11R)-11-hydroxy-7-(hydroxymethyl)-4-[(E)-4-hydroxy-4-methylpent-2-enyl]-4,11-dimethyl-8-oxocycloundeca-2,6,9-trien-1-yl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	BFHUVBRMXMQPJH-KFKQBPMQSA-N
Standard InCHI:	InChI=1S/C25H36O6/c1-18(2)16-22(28)31-21-10-14-24(5,12-7-11-23(3,4)29)13-8-19(17-26)20(27)9-15-25(21,6)30/h7-11,14-16,21,26,29-30H,12-13,17H2,1-6H3/b11-7+,14-10+,15-9+,19-8-/t21-,24+,25-/m1/s1
SMILES:	OC/C/1=C/C[C@](C)(C/C=C/C(O)(C)C)/C=C/[C@H]([C@](/C=C/C1=O)(C)O)OC(=O)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510169
PubChem CID:	643645
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]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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
NPT4162	Cell Line	NUGC	Homo sapiens	Activity	=	15.0	%	PMID[491626]

☑ 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 NPC203277 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	184
0.1-0.2	2012
0.2-0.3	7294
0.3-0.4	17362
0.4-0.5	9569
0.5-0.6	4639
0.6-0.7	1468
0.7-0.8	161
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC279532
0.9091	High Similarity	NPC161045
0.8861	High Similarity	NPC11804
0.8125	Intermediate Similarity	NPC474980
0.8056	Intermediate Similarity	NPC273600
0.7975	Intermediate Similarity	NPC473471
0.7922	Intermediate Similarity	NPC315843
0.7922	Intermediate Similarity	NPC107654
0.7867	Intermediate Similarity	NPC475982
0.7848	Intermediate Similarity	NPC125365
0.7848	Intermediate Similarity	NPC51809
0.7848	Intermediate Similarity	NPC176329
0.7848	Intermediate Similarity	NPC49302
0.7848	Intermediate Similarity	NPC474818
0.7808	Intermediate Similarity	NPC19769
0.775	Intermediate Similarity	NPC221095
0.775	Intermediate Similarity	NPC279214
0.7722	Intermediate Similarity	NPC209113
0.7722	Intermediate Similarity	NPC301207
0.7722	Intermediate Similarity	NPC127118
0.7714	Intermediate Similarity	NPC254095
0.7714	Intermediate Similarity	NPC223679
0.7703	Intermediate Similarity	NPC475675
0.7703	Intermediate Similarity	NPC201356
0.7703	Intermediate Similarity	NPC475555
0.7662	Intermediate Similarity	NPC316185
0.7662	Intermediate Similarity	NPC293114
0.7654	Intermediate Similarity	NPC99651
0.7639	Intermediate Similarity	NPC55376
0.7619	Intermediate Similarity	NPC186155
0.7619	Intermediate Similarity	NPC160517
0.7619	Intermediate Similarity	NPC78673
0.7595	Intermediate Similarity	NPC260396
0.7595	Intermediate Similarity	NPC161038
0.759	Intermediate Similarity	NPC26624
0.7571	Intermediate Similarity	NPC135863
0.7571	Intermediate Similarity	NPC293437
0.7571	Intermediate Similarity	NPC249850
0.7571	Intermediate Similarity	NPC71755
0.7571	Intermediate Similarity	NPC129150
0.7568	Intermediate Similarity	NPC96414
0.7568	Intermediate Similarity	NPC282760
0.7532	Intermediate Similarity	NPC202011
0.7529	Intermediate Similarity	NPC475034
0.75	Intermediate Similarity	NPC470705
0.75	Intermediate Similarity	NPC229799
0.75	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC44261
0.75	Intermediate Similarity	NPC284472
0.75	Intermediate Similarity	NPC286770
0.747	Intermediate Similarity	NPC112868
0.7468	Intermediate Similarity	NPC476590
0.7468	Intermediate Similarity	NPC114727
0.7467	Intermediate Similarity	NPC478101
0.7467	Intermediate Similarity	NPC146811
0.7444	Intermediate Similarity	NPC65829
0.7442	Intermediate Similarity	NPC316426
0.7442	Intermediate Similarity	NPC61527
0.7442	Intermediate Similarity	NPC315395
0.7412	Intermediate Similarity	NPC161670
0.7407	Intermediate Similarity	NPC275530
0.7397	Intermediate Similarity	NPC26810
0.7386	Intermediate Similarity	NPC79027
0.7381	Intermediate Similarity	NPC474959
0.7381	Intermediate Similarity	NPC475046
0.7381	Intermediate Similarity	NPC310450
0.7381	Intermediate Similarity	NPC11383
0.7368	Intermediate Similarity	NPC122627
0.7368	Intermediate Similarity	NPC478097
0.7368	Intermediate Similarity	NPC478100
0.7361	Intermediate Similarity	NPC302564
0.7361	Intermediate Similarity	NPC82465
0.7356	Intermediate Similarity	NPC475037
0.7342	Intermediate Similarity	NPC12815
0.7342	Intermediate Similarity	NPC215745
0.7342	Intermediate Similarity	NPC238948
0.7342	Intermediate Similarity	NPC287878
0.7333	Intermediate Similarity	NPC470123
0.7333	Intermediate Similarity	NPC282644
0.7333	Intermediate Similarity	NPC478098
0.7333	Intermediate Similarity	NPC29798
0.7333	Intermediate Similarity	NPC478099
0.7326	Intermediate Similarity	NPC471494
0.7326	Intermediate Similarity	NPC261380
0.7324	Intermediate Similarity	NPC294938
0.7317	Intermediate Similarity	NPC474816
0.7317	Intermediate Similarity	NPC209135
0.7317	Intermediate Similarity	NPC318481
0.7308	Intermediate Similarity	NPC469660
0.7308	Intermediate Similarity	NPC59558
0.7308	Intermediate Similarity	NPC473361
0.7308	Intermediate Similarity	NPC329904
0.7297	Intermediate Similarity	NPC473737
0.7294	Intermediate Similarity	NPC474809
0.7284	Intermediate Similarity	NPC256640
0.7284	Intermediate Similarity	NPC16279
0.7284	Intermediate Similarity	NPC205615
0.7262	Intermediate Similarity	NPC150502
0.725	Intermediate Similarity	NPC160540
0.7241	Intermediate Similarity	NPC311163
0.7237	Intermediate Similarity	NPC276299
0.7222	Intermediate Similarity	NPC21946
0.7209	Intermediate Similarity	NPC475035
0.7209	Intermediate Similarity	NPC31086
0.7209	Intermediate Similarity	NPC474865
0.72	Intermediate Similarity	NPC470808
0.7195	Intermediate Similarity	NPC262747
0.7195	Intermediate Similarity	NPC475711
0.7191	Intermediate Similarity	NPC87306
0.7191	Intermediate Similarity	NPC83423
0.7188	Intermediate Similarity	NPC472755
0.7179	Intermediate Similarity	NPC151481
0.7176	Intermediate Similarity	NPC85772
0.7162	Intermediate Similarity	NPC263732
0.716	Intermediate Similarity	NPC478195
0.716	Intermediate Similarity	NPC478194
0.716	Intermediate Similarity	NPC478196
0.716	Intermediate Similarity	NPC478192
0.716	Intermediate Similarity	NPC478193
0.716	Intermediate Similarity	NPC478191
0.7158	Intermediate Similarity	NPC472753
0.7143	Intermediate Similarity	NPC121374
0.7143	Intermediate Similarity	NPC469692
0.7143	Intermediate Similarity	NPC469645
0.7125	Intermediate Similarity	NPC284006
0.7123	Intermediate Similarity	NPC322186
0.7123	Intermediate Similarity	NPC97570
0.7111	Intermediate Similarity	NPC473455
0.7111	Intermediate Similarity	NPC145666
0.7111	Intermediate Similarity	NPC475879
0.7108	Intermediate Similarity	NPC182292
0.7108	Intermediate Similarity	NPC248775
0.7093	Intermediate Similarity	NPC49208
0.7093	Intermediate Similarity	NPC23748
0.7093	Intermediate Similarity	NPC315559
0.7089	Intermediate Similarity	NPC4299
0.7089	Intermediate Similarity	NPC476037
0.7083	Intermediate Similarity	NPC472754
0.7079	Intermediate Similarity	NPC153570
0.7079	Intermediate Similarity	NPC287089
0.7073	Intermediate Similarity	NPC4492
0.7073	Intermediate Similarity	NPC51391
0.7067	Intermediate Similarity	NPC68110
0.7065	Intermediate Similarity	NPC121825
0.7059	Intermediate Similarity	NPC475944
0.7051	Intermediate Similarity	NPC310210
0.7051	Intermediate Similarity	NPC63873
0.7045	Intermediate Similarity	NPC469910
0.7037	Intermediate Similarity	NPC470686
0.7027	Intermediate Similarity	NPC26223
0.7027	Intermediate Similarity	NPC79756
0.7024	Intermediate Similarity	NPC470149
0.7024	Intermediate Similarity	NPC471537
0.7024	Intermediate Similarity	NPC470148
0.7024	Intermediate Similarity	NPC180725
0.7024	Intermediate Similarity	NPC1180
0.7021	Intermediate Similarity	NPC245521
0.7011	Intermediate Similarity	NPC266718
0.7011	Intermediate Similarity	NPC219966
0.7011	Intermediate Similarity	NPC243618
0.7011	Intermediate Similarity	NPC70424
0.7	Intermediate Similarity	NPC477087
0.7	Intermediate Similarity	NPC130359
0.7	Intermediate Similarity	NPC477086
0.7	Intermediate Similarity	NPC14901
0.7	Intermediate Similarity	NPC47951
0.6989	Remote Similarity	NPC214694
0.6988	Remote Similarity	NPC474278
0.6977	Remote Similarity	NPC323251
0.6977	Remote Similarity	NPC474291
0.6977	Remote Similarity	NPC471296
0.6977	Remote Similarity	NPC313677
0.6966	Remote Similarity	NPC45409
0.6966	Remote Similarity	NPC473248
0.6966	Remote Similarity	NPC72513
0.6962	Remote Similarity	NPC476591
0.6962	Remote Similarity	NPC101622
0.6962	Remote Similarity	NPC88877
0.6951	Remote Similarity	NPC473582
0.6947	Remote Similarity	NPC124512
0.6947	Remote Similarity	NPC316598
0.6947	Remote Similarity	NPC278386
0.6947	Remote Similarity	NPC161855
0.6947	Remote Similarity	NPC159763
0.6947	Remote Similarity	NPC475653
0.6944	Remote Similarity	NPC230296
0.6941	Remote Similarity	NPC470147
0.6941	Remote Similarity	NPC133226
0.6941	Remote Similarity	NPC47653
0.6939	Remote Similarity	NPC472756
0.6933	Remote Similarity	NPC151648
0.6932	Remote Similarity	NPC470755
0.6932	Remote Similarity	NPC470124
0.6932	Remote Similarity	NPC21469
0.6931	Remote Similarity	NPC29133
0.6923	Remote Similarity	NPC473448
0.6923	Remote Similarity	NPC106613
0.6923	Remote Similarity	NPC203335
0.6923	Remote Similarity	NPC474761
0.6923	Remote Similarity	NPC3952

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 NPC203277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2536
0.2-0.3	4093
0.3-0.4	1789
0.4-0.5	460
0.5-0.6	93
0.6-0.7	22
0.7-0.8	0
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
0.7111	Intermediate Similarity	NPD5785	Approved
0.6947	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD7838	Discovery
0.6818	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5209	Approved
0.6765	Remote Similarity	NPD6371	Approved
0.6598	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6698	Approved
0.6559	Remote Similarity	NPD46	Approved
0.6556	Remote Similarity	NPD5363	Approved
0.6542	Remote Similarity	NPD7115	Discovery
0.6533	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6109	Phase 1
0.6489	Remote Similarity	NPD7983	Approved
0.6479	Remote Similarity	NPD6927	Phase 3
0.6465	Remote Similarity	NPD5344	Discontinued
0.6458	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4252	Approved
0.6322	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7637	Suspended
0.6222	Remote Similarity	NPD4269	Approved
0.6222	Remote Similarity	NPD4270	Approved
0.618	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7154	Phase 3
0.6154	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5786	Approved
0.6125	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5369	Approved
0.6104	Remote Similarity	NPD69	Approved
0.6104	Remote Similarity	NPD9119	Approved
0.6098	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.5978	Remote Similarity	NPD5362	Discontinued
0.5974	Remote Similarity	NPD9118	Approved
0.5972	Remote Similarity	NPD4220	Pre-registration
0.5955	Remote Similarity	NPD4268	Approved
0.5955	Remote Similarity	NPD4271	Approved
0.5943	Remote Similarity	NPD6686	Approved
0.5938	Remote Similarity	NPD5370	Suspended
0.5918	Remote Similarity	NPD5779	Approved
0.5918	Remote Similarity	NPD5778	Approved
0.59	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7640	Approved
0.5882	Remote Similarity	NPD7639	Approved
0.5875	Remote Similarity	NPD4192	Approved
0.5875	Remote Similarity	NPD4194	Approved
0.5875	Remote Similarity	NPD4193	Approved
0.5875	Remote Similarity	NPD4191	Approved
0.5851	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4756	Discovery
0.5824	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6411	Approved
0.5816	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5331	Approved
0.5806	Remote Similarity	NPD5332	Approved
0.5795	Remote Similarity	NPD8039	Approved
0.5784	Remote Similarity	NPD7638	Approved
0.5775	Remote Similarity	NPD4265	Approved
0.5761	Remote Similarity	NPD4790	Discontinued
0.5743	Remote Similarity	NPD7839	Suspended
0.5732	Remote Similarity	NPD3197	Phase 1
0.5729	Remote Similarity	NPD4251	Approved
0.5729	Remote Similarity	NPD4250	Approved
0.5699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD1694	Approved
0.5636	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD6097	Approved
0.5634	Remote Similarity	NPD6096	Approved
0.5625	Remote Similarity	NPD4249	Approved
0.5616	Remote Similarity	NPD5343	Approved
0.5612	Remote Similarity	NPD6101	Approved
0.5612	Remote Similarity	NPD5764	Clinical (unspecified phase)

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