NPASS Compound

Structure

CID55508 OpenBabel06191715392D 23 25 0 0 1 0 0 0 0 0999 V2000 0.7615 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7026 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 -1.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -1.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5686 2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 0.5055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4347 2.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 1.0055 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 12 1 0 0 0 0 2 13 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 12 19 1 6 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 1 0 0 0 15 17 1 0 0 0 0 15 22 1 1 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 18 19 1 6 0 0 0 19 11 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.21
Volume:	341.399
LogP:	3.743
LogD:	3.37
LogS:	-4.415
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	4.564
Fsp3:	0.895
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.696
MDCK Permeability:	2.466392470523715e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	68.01647186279297%
Volume Distribution (VD):	0.683
Pgp-substrate:	32.28363037109375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.688
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.238
CYP3A4-inhibitor:	0.526
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	6.367
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.923
Carcinogencity:	0.305
Eye Corrosion:	0.677
Eye Irritation:	0.194
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC55508

Natural Product ID:	NPC55508
*Common Name:**	Vitedoin B
IUPAC Name:	[(2S,4aS,5R,6R,8aS)-1,1,4a,6-tetramethyl-5'-oxospiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxolane]-2-yl] acetate
Synonyms:	vitedoin B
Standard InCHIKey:	HBMMUGYRQKNIBQ-SZQWKIALSA-N
Standard InCHI:	InChI=1S/C19H30O4/c1-12-6-7-14-17(3,4)15(22-13(2)20)8-10-18(14,5)19(12)11-9-16(21)23-19/h12,14-15H,6-11H2,1-5H3/t12-,14+,15+,18+,19-/m1/s1
SMILES:	C[C@@H]1CC[C@H]2C(C)(C)[C@H](CC[C@]2(C)[C@]21CCC(=O)O2)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505801
PubChem CID:	11771639
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[534595]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[534595]

☑ 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 NPC55508 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	354
0.1-0.2	3255
0.2-0.3	10130
0.3-0.4	13045
0.4-0.5	5617
0.5-0.6	6425
0.6-0.7	3266
0.7-0.8	547
0.8-0.85	41
0.85-0.9	12
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC109510
0.9189	High Similarity	NPC125366
0.9189	High Similarity	NPC134227
0.8971	High Similarity	NPC84562
0.8784	High Similarity	NPC143250
0.8718	High Similarity	NPC65133
0.8608	High Similarity	NPC477445
0.8571	High Similarity	NPC475743
0.8553	High Similarity	NPC73013
0.8533	High Similarity	NPC307865
0.8493	Intermediate Similarity	NPC474755
0.8481	Intermediate Similarity	NPC473299
0.8481	Intermediate Similarity	NPC477434
0.8382	Intermediate Similarity	NPC306750
0.8354	Intermediate Similarity	NPC15091
0.8293	Intermediate Similarity	NPC221993
0.8293	Intermediate Similarity	NPC471221
0.8272	Intermediate Similarity	NPC477441
0.8235	Intermediate Similarity	NPC478126
0.8228	Intermediate Similarity	NPC13494
0.8171	Intermediate Similarity	NPC175293
0.8158	Intermediate Similarity	NPC92489
0.8158	Intermediate Similarity	NPC471046
0.8133	Intermediate Similarity	NPC96759
0.8101	Intermediate Similarity	NPC58631
0.8101	Intermediate Similarity	NPC48756
0.8101	Intermediate Similarity	NPC280781
0.8077	Intermediate Similarity	NPC201276
0.8077	Intermediate Similarity	NPC80891
0.8077	Intermediate Similarity	NPC474754
0.8072	Intermediate Similarity	NPC476435
0.8056	Intermediate Similarity	NPC41542
0.8052	Intermediate Similarity	NPC471151
0.8025	Intermediate Similarity	NPC181871
0.8025	Intermediate Similarity	NPC97505
0.8025	Intermediate Similarity	NPC473336
0.8025	Intermediate Similarity	NPC471044
0.8025	Intermediate Similarity	NPC9060
0.8	Intermediate Similarity	NPC216137
0.7976	Intermediate Similarity	NPC471459
0.7976	Intermediate Similarity	NPC477443
0.7976	Intermediate Similarity	NPC67653
0.7976	Intermediate Similarity	NPC477440
0.7971	Intermediate Similarity	NPC204173
0.7949	Intermediate Similarity	NPC80089
0.7949	Intermediate Similarity	NPC224802
0.7949	Intermediate Similarity	NPC324700
0.7949	Intermediate Similarity	NPC171426
0.7949	Intermediate Similarity	NPC34046
0.7927	Intermediate Similarity	NPC473350
0.7927	Intermediate Similarity	NPC474572
0.7882	Intermediate Similarity	NPC477433
0.7882	Intermediate Similarity	NPC475776
0.7882	Intermediate Similarity	NPC185529
0.7882	Intermediate Similarity	NPC477444
0.7882	Intermediate Similarity	NPC472146
0.7882	Intermediate Similarity	NPC470114
0.7882	Intermediate Similarity	NPC477442
0.7875	Intermediate Similarity	NPC329490
0.7875	Intermediate Similarity	NPC328639
0.7848	Intermediate Similarity	NPC477287
0.7838	Intermediate Similarity	NPC295788
0.7816	Intermediate Similarity	NPC470424
0.7805	Intermediate Similarity	NPC219535
0.7805	Intermediate Similarity	NPC237938
0.7792	Intermediate Similarity	NPC186851
0.7791	Intermediate Similarity	NPC475878
0.7778	Intermediate Similarity	NPC242771
0.7778	Intermediate Similarity	NPC311642
0.7778	Intermediate Similarity	NPC164289
0.7778	Intermediate Similarity	NPC230047
0.7778	Intermediate Similarity	NPC102156
0.7778	Intermediate Similarity	NPC19311
0.7778	Intermediate Similarity	NPC148740
0.7778	Intermediate Similarity	NPC100366
0.7765	Intermediate Similarity	NPC200580
0.7763	Intermediate Similarity	NPC123122
0.775	Intermediate Similarity	NPC471216
0.775	Intermediate Similarity	NPC472943
0.775	Intermediate Similarity	NPC472951
0.775	Intermediate Similarity	NPC471217
0.775	Intermediate Similarity	NPC60568
0.775	Intermediate Similarity	NPC1882
0.775	Intermediate Similarity	NPC261616
0.7738	Intermediate Similarity	NPC239938
0.7738	Intermediate Similarity	NPC470920
0.7727	Intermediate Similarity	NPC82633
0.7722	Intermediate Similarity	NPC31031
0.7722	Intermediate Similarity	NPC243594
0.7711	Intermediate Similarity	NPC62572
0.7711	Intermediate Similarity	NPC477205
0.7701	Intermediate Similarity	NPC474379
0.7701	Intermediate Similarity	NPC147272
0.7692	Intermediate Similarity	NPC4209
0.7692	Intermediate Similarity	NPC474020
0.7683	Intermediate Similarity	NPC476721
0.7674	Intermediate Similarity	NPC18536
0.7674	Intermediate Similarity	NPC50443
0.7654	Intermediate Similarity	NPC71541
0.7654	Intermediate Similarity	NPC470154
0.7654	Intermediate Similarity	NPC271572
0.7654	Intermediate Similarity	NPC476071
0.7654	Intermediate Similarity	NPC470156
0.7654	Intermediate Similarity	NPC475951
0.7654	Intermediate Similarity	NPC474870
0.7647	Intermediate Similarity	NPC473319
0.7647	Intermediate Similarity	NPC3032
0.7647	Intermediate Similarity	NPC476379
0.7647	Intermediate Similarity	NPC131104
0.7647	Intermediate Similarity	NPC236459
0.764	Intermediate Similarity	NPC473964
0.764	Intermediate Similarity	NPC235109
0.764	Intermediate Similarity	NPC163685
0.764	Intermediate Similarity	NPC116683
0.7632	Intermediate Similarity	NPC197701
0.7625	Intermediate Similarity	NPC476176
0.7619	Intermediate Similarity	NPC248216
0.7619	Intermediate Similarity	NPC474008
0.7619	Intermediate Similarity	NPC476717
0.7619	Intermediate Similarity	NPC83242
0.7614	Intermediate Similarity	NPC477495
0.76	Intermediate Similarity	NPC178541
0.7595	Intermediate Similarity	NPC212453
0.7595	Intermediate Similarity	NPC317913
0.7595	Intermediate Similarity	NPC207010
0.759	Intermediate Similarity	NPC79308
0.7568	Intermediate Similarity	NPC476928
0.7564	Intermediate Similarity	NPC212733
0.7561	Intermediate Similarity	NPC477284
0.7561	Intermediate Similarity	NPC226988
0.7561	Intermediate Similarity	NPC477446
0.7561	Intermediate Similarity	NPC61107
0.7561	Intermediate Similarity	NPC121121
0.7561	Intermediate Similarity	NPC470155
0.7561	Intermediate Similarity	NPC477447
0.7561	Intermediate Similarity	NPC289486
0.7558	Intermediate Similarity	NPC61688
0.7558	Intermediate Similarity	NPC194642
0.7558	Intermediate Similarity	NPC472233
0.7558	Intermediate Similarity	NPC116620
0.7558	Intermediate Similarity	NPC472234
0.7558	Intermediate Similarity	NPC471043
0.7556	Intermediate Similarity	NPC266417
0.7556	Intermediate Similarity	NPC473963
0.7556	Intermediate Similarity	NPC474921
0.7532	Intermediate Similarity	NPC475230
0.7532	Intermediate Similarity	NPC476718
0.7531	Intermediate Similarity	NPC170038
0.7531	Intermediate Similarity	NPC475456
0.7531	Intermediate Similarity	NPC474714
0.7531	Intermediate Similarity	NPC477851
0.7528	Intermediate Similarity	NPC259042
0.7528	Intermediate Similarity	NPC157686
0.75	Intermediate Similarity	NPC472608
0.75	Intermediate Similarity	NPC476715
0.75	Intermediate Similarity	NPC476189
0.75	Intermediate Similarity	NPC252483
0.75	Intermediate Similarity	NPC191345
0.7473	Intermediate Similarity	NPC472144
0.7473	Intermediate Similarity	NPC474724
0.7471	Intermediate Similarity	NPC475211
0.7471	Intermediate Similarity	NPC77756
0.7471	Intermediate Similarity	NPC88337
0.7444	Intermediate Similarity	NPC193785
0.7444	Intermediate Similarity	NPC256227
0.7444	Intermediate Similarity	NPC475785
0.7444	Intermediate Similarity	NPC475765
0.7444	Intermediate Similarity	NPC93245
0.7442	Intermediate Similarity	NPC477614
0.7442	Intermediate Similarity	NPC226491
0.7439	Intermediate Similarity	NPC12933
0.7439	Intermediate Similarity	NPC209318
0.7439	Intermediate Similarity	NPC190940
0.7439	Intermediate Similarity	NPC223330
0.7439	Intermediate Similarity	NPC50658
0.7439	Intermediate Similarity	NPC73515
0.7436	Intermediate Similarity	NPC167702
0.7436	Intermediate Similarity	NPC280026
0.7416	Intermediate Similarity	NPC469596
0.7416	Intermediate Similarity	NPC471446
0.7416	Intermediate Similarity	NPC224410
0.7416	Intermediate Similarity	NPC225474
0.7416	Intermediate Similarity	NPC473434
0.7416	Intermediate Similarity	NPC100257
0.7416	Intermediate Similarity	NPC148000
0.7416	Intermediate Similarity	NPC474841
0.7412	Intermediate Similarity	NPC228593
0.7412	Intermediate Similarity	NPC80700
0.7412	Intermediate Similarity	NPC235196
0.7412	Intermediate Similarity	NPC472272
0.7407	Intermediate Similarity	NPC320144
0.7407	Intermediate Similarity	NPC118987
0.7407	Intermediate Similarity	NPC220379
0.7403	Intermediate Similarity	NPC89310
0.7403	Intermediate Similarity	NPC478227
0.7403	Intermediate Similarity	NPC469940
0.7391	Intermediate Similarity	NPC477656
0.7386	Intermediate Similarity	NPC198054
0.7386	Intermediate Similarity	NPC470230
0.7386	Intermediate Similarity	NPC52756

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 NPC55508 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	3592
0.2-0.3	3416
0.3-0.4	1060
0.4-0.5	313
0.5-0.6	259
0.6-0.7	114
0.7-0.8	15
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7949	Intermediate Similarity	NPD6115	Approved
0.7949	Intermediate Similarity	NPD6118	Approved
0.7949	Intermediate Similarity	NPD6114	Approved
0.7949	Intermediate Similarity	NPD6697	Approved
0.7692	Intermediate Similarity	NPD6117	Approved
0.7632	Intermediate Similarity	NPD5777	Approved
0.7595	Intermediate Similarity	NPD6116	Phase 1
0.7436	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3703	Phase 2
0.7342	Intermediate Similarity	NPD3702	Approved
0.7229	Intermediate Similarity	NPD1779	Approved
0.7229	Intermediate Similarity	NPD1780	Approved
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD229	Approved
0.701	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD8034	Phase 2
0.7	Intermediate Similarity	NPD8035	Phase 2
0.6974	Remote Similarity	NPD4224	Phase 2
0.6962	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5360	Phase 3
0.6795	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD1700	Approved
0.6768	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6081	Approved
0.6709	Remote Similarity	NPD3698	Phase 2
0.6705	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3669	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6625	Remote Similarity	NPD4244	Approved
0.6625	Remote Similarity	NPD4245	Approved
0.6623	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7638	Approved
0.6559	Remote Similarity	NPD6399	Phase 3
0.6543	Remote Similarity	NPD4758	Discontinued
0.6535	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1694	Approved
0.6495	Remote Similarity	NPD7639	Approved
0.6495	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3671	Phase 1
0.6458	Remote Similarity	NPD7902	Approved
0.6444	Remote Similarity	NPD7334	Approved
0.6444	Remote Similarity	NPD6409	Approved
0.6444	Remote Similarity	NPD5330	Approved
0.6444	Remote Similarity	NPD6684	Approved
0.6444	Remote Similarity	NPD7146	Approved
0.6444	Remote Similarity	NPD7521	Approved
0.642	Remote Similarity	NPD4789	Approved
0.6374	Remote Similarity	NPD3573	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7632	Discontinued
0.6327	Remote Similarity	NPD8418	Phase 2
0.6322	Remote Similarity	NPD6928	Phase 2
0.6316	Remote Similarity	NPD6001	Approved
0.6311	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6903	Approved
0.6304	Remote Similarity	NPD6672	Approved
0.6304	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5737	Approved
0.6296	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3726	Approved
0.6296	Remote Similarity	NPD3725	Approved
0.6279	Remote Similarity	NPD4802	Phase 2
0.6279	Remote Similarity	NPD4238	Approved
0.6279	Remote Similarity	NPD5364	Discontinued
0.6277	Remote Similarity	NPD7515	Phase 2
0.6264	Remote Similarity	NPD3618	Phase 1
0.6238	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2687	Approved
0.622	Remote Similarity	NPD2686	Approved
0.622	Remote Similarity	NPD2254	Approved
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.6164	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6372	Approved
0.6117	Remote Similarity	NPD5697	Approved
0.6117	Remote Similarity	NPD5701	Approved
0.6087	Remote Similarity	NPD6098	Approved
0.6075	Remote Similarity	NPD8133	Approved
0.6075	Remote Similarity	NPD4632	Approved
0.6064	Remote Similarity	NPD6080	Approved
0.6064	Remote Similarity	NPD6904	Approved
0.6064	Remote Similarity	NPD6673	Approved
0.6061	Remote Similarity	NPD4225	Approved
0.6061	Remote Similarity	NPD5696	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD7320	Approved
0.6058	Remote Similarity	NPD6011	Approved
0.6044	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD6650	Approved
0.6038	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6012	Approved
0.5974	Remote Similarity	NPD3198	Approved
0.596	Remote Similarity	NPD6083	Phase 2
0.596	Remote Similarity	NPD6084	Phase 2
0.5957	Remote Similarity	NPD5208	Approved
0.5943	Remote Similarity	NPD7102	Approved
0.5943	Remote Similarity	NPD7290	Approved
0.5943	Remote Similarity	NPD6883	Approved
0.5938	Remote Similarity	NPD5693	Phase 1
0.5918	Remote Similarity	NPD5695	Phase 3
0.5914	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6009	Approved
0.5895	Remote Similarity	NPD5328	Approved
0.5893	Remote Similarity	NPD6319	Approved
0.5888	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6617	Approved
0.5888	Remote Similarity	NPD6847	Approved
0.5888	Remote Similarity	NPD8130	Phase 1
0.5888	Remote Similarity	NPD6869	Approved
0.5876	Remote Similarity	NPD4202	Approved
0.5875	Remote Similarity	NPD7909	Approved
0.5875	Remote Similarity	NPD371	Approved
0.587	Remote Similarity	NPD4786	Approved
0.5859	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4697	Phase 3
0.5841	Remote Similarity	NPD6921	Approved
0.5841	Remote Similarity	NPD5983	Phase 2
0.5833	Remote Similarity	NPD4787	Phase 1
0.5833	Remote Similarity	NPD8297	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD5692	Phase 3
0.5826	Remote Similarity	NPD7492	Approved
0.5818	Remote Similarity	NPD6940	Discontinued
0.5814	Remote Similarity	NPD1810	Approved
0.5814	Remote Similarity	NPD1811	Approved
0.58	Remote Similarity	NPD4755	Approved
0.5797	Remote Similarity	NPD2699	Approved
0.5795	Remote Similarity	NPD8143	Approved
0.5795	Remote Similarity	NPD8144	Approved
0.5776	Remote Similarity	NPD6616	Approved
0.5775	Remote Similarity	NPD2266	Phase 2
0.5773	Remote Similarity	NPD6050	Approved
0.5773	Remote Similarity	NPD6079	Approved
0.5773	Remote Similarity	NPD5694	Approved
0.5766	Remote Similarity	NPD7115	Discovery
0.5761	Remote Similarity	NPD4788	Approved
0.5755	Remote Similarity	NPD6686	Approved
0.5752	Remote Similarity	NPD6054	Approved
0.5752	Remote Similarity	NPD6059	Approved
0.5745	Remote Similarity	NPD8308	Discontinued
0.5739	Remote Similarity	NPD7604	Phase 2
0.5735	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6051	Approved
0.5726	Remote Similarity	NPD8293	Discontinued
0.5726	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD8171	Discontinued
0.5702	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6016	Approved
0.5702	Remote Similarity	NPD6015	Approved
0.57	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5221	Approved
0.57	Remote Similarity	NPD5222	Approved
0.5699	Remote Similarity	NPD3666	Approved
0.5699	Remote Similarity	NPD3665	Phase 1
0.5699	Remote Similarity	NPD3133	Approved
0.5686	Remote Similarity	NPD4700	Approved
0.5686	Remote Similarity	NPD5286	Approved
0.5686	Remote Similarity	NPD5285	Approved
0.5686	Remote Similarity	NPD4696	Approved
0.5678	Remote Similarity	NPD7736	Approved
0.5676	Remote Similarity	NPD6274	Approved
0.5673	Remote Similarity	NPD6052	Approved
0.566	Remote Similarity	NPD6412	Phase 2
0.5657	Remote Similarity	NPD5282	Discontinued
0.5652	Remote Similarity	NPD6370	Approved
0.5652	Remote Similarity	NPD5988	Approved
0.5647	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5173	Approved
0.5641	Remote Similarity	NPD7507	Approved
0.5641	Remote Similarity	NPD6336	Discontinued
0.5631	Remote Similarity	NPD5223	Approved
0.5625	Remote Similarity	NPD6317	Approved
0.5612	Remote Similarity	NPD5281	Approved
0.5612	Remote Similarity	NPD5284	Approved
0.5612	Remote Similarity	NPD6411	Approved
0.5604	Remote Similarity	NPD7525	Registered
0.5603	Remote Similarity	NPD8328	Phase 3
0.56	Remote Similarity	NPD7991	Discontinued
0.56	Remote Similarity	NPD5654	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