NPASS Compound

Structure

CID109510 OpenBabel06191715462D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.0475 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0116 -0.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5116 -0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -2.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -1.9067 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 -1.7796 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5116 2.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 0.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5116 -0.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.9067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3776 2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 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 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 19 1 1 0 0 0 13 20 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 6 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 6 0 0 0 18 19 1 1 0 0 0 19 10 1 6 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.21
Volume:	341.399
LogP:	3.806
LogD:	3.477
LogS:	-4.55
# 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:	4.764
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:	-4.813
MDCK Permeability:	2.3535847503808327e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.559
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	79.49925994873047%
Volume Distribution (VD):	1.009
Pgp-substrate:	27.522581100463867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.27
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.516
CYP2C9-substrate:	0.197
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.384

ADMET: Excretion

Clearance (CL):	5.236
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.666
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.219
Skin Sensitization:	0.936
Carcinogencity:	0.245
Eye Corrosion:	0.276
Eye Irritation:	0.199
Respiratory Toxicity:	0.691

Download Data

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

Natural Product: NPC109510

Natural Product ID:	NPC109510
*Common Name:**	Trisnor-Gamma-Lactone
IUPAC Name:	[(1R,3R,4R,4aS,8aS)-3,4a,8,8-tetramethyl-5'-oxospiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,2'-oxolane]-1-yl] acetate
Synonyms:	Trisnor-Gamma-Lactone
Standard InCHIKey:	HXILYTQMWOYCAT-IONYDWJHSA-N
Standard InCHI:	InChI=1S/C19H30O4/c1-12-11-14(22-13(2)20)16-17(3,4)8-6-9-18(16,5)19(12)10-7-15(21)23-19/h12,14,16H,6-11H2,1-5H3/t12-,14-,16+,18+,19-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H](C)[C@@]2([C@@]3([C@@H]1C(C)(C)CCC3)C)CCC(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464481
PubChem CID:	21668661
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]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
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]
NPO15454	Vitex rotundifolia	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]

☑ 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
GI50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	GI50	>	5.0	ug.mL-1	PMID[469462]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	>	5.0	ug.mL-1	PMID[469462]

☑ 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 NPC109510 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	342
0.1-0.2	3257
0.2-0.3	12300
0.3-0.4	11245
0.4-0.5	5814
0.5-0.6	6388
0.6-0.7	2889
0.7-0.8	419
0.8-0.85	30
0.85-0.9	9
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC55508
0.9167	High Similarity	NPC307865
0.9104	High Similarity	NPC84562
0.9054	High Similarity	NPC125366
0.9054	High Similarity	NPC134227
0.8873	High Similarity	NPC474755
0.8667	High Similarity	NPC73013
0.859	High Similarity	NPC65133
0.8507	High Similarity	NPC306750
0.8421	Intermediate Similarity	NPC474754
0.84	Intermediate Similarity	NPC143250
0.8358	Intermediate Similarity	NPC478126
0.8333	Intermediate Similarity	NPC13494
0.8267	Intermediate Similarity	NPC471046
0.8267	Intermediate Similarity	NPC92489
0.8205	Intermediate Similarity	NPC280781
0.8205	Intermediate Similarity	NPC475743
0.8205	Intermediate Similarity	NPC48756
0.8205	Intermediate Similarity	NPC58631
0.8171	Intermediate Similarity	NPC471221
0.8169	Intermediate Similarity	NPC41542
0.8158	Intermediate Similarity	NPC471151
0.8148	Intermediate Similarity	NPC477441
0.8125	Intermediate Similarity	NPC473299
0.8088	Intermediate Similarity	NPC204173
0.8025	Intermediate Similarity	NPC477445
0.8	Intermediate Similarity	NPC15091
0.7975	Intermediate Similarity	NPC271572
0.7975	Intermediate Similarity	NPC475951
0.7975	Intermediate Similarity	NPC474870
0.7952	Intermediate Similarity	NPC221993
0.7945	Intermediate Similarity	NPC295788
0.7922	Intermediate Similarity	NPC207010
0.7922	Intermediate Similarity	NPC317913
0.7917	Intermediate Similarity	NPC476928
0.7901	Intermediate Similarity	NPC79308
0.7901	Intermediate Similarity	NPC477434
0.7887	Intermediate Similarity	NPC230047
0.7887	Intermediate Similarity	NPC19311
0.7882	Intermediate Similarity	NPC216137
0.7857	Intermediate Similarity	NPC472234
0.7857	Intermediate Similarity	NPC477440
0.7857	Intermediate Similarity	NPC477443
0.7857	Intermediate Similarity	NPC472233
0.7848	Intermediate Similarity	NPC261616
0.7821	Intermediate Similarity	NPC31031
0.7821	Intermediate Similarity	NPC472608
0.7821	Intermediate Similarity	NPC243594
0.7805	Intermediate Similarity	NPC62572
0.7792	Intermediate Similarity	NPC4209
0.7765	Intermediate Similarity	NPC477444
0.7765	Intermediate Similarity	NPC477442
0.7765	Intermediate Similarity	NPC477433
0.775	Intermediate Similarity	NPC209318
0.775	Intermediate Similarity	NPC223330
0.7733	Intermediate Similarity	NPC197701
0.7722	Intermediate Similarity	NPC80891
0.7722	Intermediate Similarity	NPC201276
0.7703	Intermediate Similarity	NPC178541
0.7683	Intermediate Similarity	NPC34984
0.7683	Intermediate Similarity	NPC25037
0.7662	Intermediate Similarity	NPC212733
0.7654	Intermediate Similarity	NPC289486
0.7654	Intermediate Similarity	NPC61107
0.7654	Intermediate Similarity	NPC226988
0.7647	Intermediate Similarity	NPC67653
0.7647	Intermediate Similarity	NPC471459
0.7632	Intermediate Similarity	NPC475230
0.7625	Intermediate Similarity	NPC170038
0.7625	Intermediate Similarity	NPC1882
0.7619	Intermediate Similarity	NPC175293
0.7595	Intermediate Similarity	NPC80089
0.7595	Intermediate Similarity	NPC34046
0.7595	Intermediate Similarity	NPC224802
0.7595	Intermediate Similarity	NPC171426
0.7595	Intermediate Similarity	NPC324700
0.7586	Intermediate Similarity	NPC472232
0.7586	Intermediate Similarity	NPC147272
0.7586	Intermediate Similarity	NPC472231
0.7558	Intermediate Similarity	NPC470114
0.7558	Intermediate Similarity	NPC475776
0.7558	Intermediate Similarity	NPC185529
0.7558	Intermediate Similarity	NPC472146
0.7532	Intermediate Similarity	NPC96759
0.7532	Intermediate Similarity	NPC167702
0.7532	Intermediate Similarity	NPC280026
0.7531	Intermediate Similarity	NPC328639
0.7531	Intermediate Similarity	NPC470154
0.7531	Intermediate Similarity	NPC12933
0.7531	Intermediate Similarity	NPC329490
0.7531	Intermediate Similarity	NPC470156
0.7531	Intermediate Similarity	NPC50658
0.7531	Intermediate Similarity	NPC71541
0.7529	Intermediate Similarity	NPC476379
0.7529	Intermediate Similarity	NPC476435
0.7528	Intermediate Similarity	NPC473964
0.75	Intermediate Similarity	NPC478227
0.75	Intermediate Similarity	NPC118987
0.75	Intermediate Similarity	NPC469940
0.75	Intermediate Similarity	NPC320144
0.75	Intermediate Similarity	NPC248216
0.75	Intermediate Similarity	NPC477495
0.75	Intermediate Similarity	NPC89310
0.75	Intermediate Similarity	NPC309127
0.75	Intermediate Similarity	NPC247877
0.75	Intermediate Similarity	NPC477287
0.75	Intermediate Similarity	NPC470424
0.75	Intermediate Similarity	NPC120395
0.7471	Intermediate Similarity	NPC475878
0.747	Intermediate Similarity	NPC319909
0.747	Intermediate Similarity	NPC9060
0.747	Intermediate Similarity	NPC473336
0.747	Intermediate Similarity	NPC97505
0.747	Intermediate Similarity	NPC470011
0.747	Intermediate Similarity	NPC139566
0.747	Intermediate Similarity	NPC471044
0.747	Intermediate Similarity	NPC181871
0.7468	Intermediate Similarity	NPC143133
0.7468	Intermediate Similarity	NPC474404
0.7468	Intermediate Similarity	NPC298168
0.7467	Intermediate Similarity	NPC196197
0.7444	Intermediate Similarity	NPC266417
0.7444	Intermediate Similarity	NPC473963
0.7444	Intermediate Similarity	NPC474921
0.7442	Intermediate Similarity	NPC253618
0.7442	Intermediate Similarity	NPC200580
0.7442	Intermediate Similarity	NPC194642
0.7442	Intermediate Similarity	NPC77001
0.7439	Intermediate Similarity	NPC477446
0.7439	Intermediate Similarity	NPC164289
0.7439	Intermediate Similarity	NPC470155
0.7439	Intermediate Similarity	NPC121121
0.7439	Intermediate Similarity	NPC242771
0.7439	Intermediate Similarity	NPC311642
0.7439	Intermediate Similarity	NPC102156
0.7439	Intermediate Similarity	NPC148740
0.7439	Intermediate Similarity	NPC100366
0.7439	Intermediate Similarity	NPC477447
0.7436	Intermediate Similarity	NPC179858
0.7436	Intermediate Similarity	NPC478105
0.7412	Intermediate Similarity	NPC305029
0.7412	Intermediate Similarity	NPC239938
0.7407	Intermediate Similarity	NPC471217
0.7407	Intermediate Similarity	NPC472943
0.7407	Intermediate Similarity	NPC471216
0.7407	Intermediate Similarity	NPC472951
0.7407	Intermediate Similarity	NPC60568
0.7403	Intermediate Similarity	NPC123122
0.7386	Intermediate Similarity	NPC472147
0.7386	Intermediate Similarity	NPC474379
0.7386	Intermediate Similarity	NPC472148
0.7381	Intermediate Similarity	NPC473350
0.7381	Intermediate Similarity	NPC98270
0.7381	Intermediate Similarity	NPC474572
0.7375	Intermediate Similarity	NPC475725
0.7375	Intermediate Similarity	NPC185465
0.7375	Intermediate Similarity	NPC329117
0.7356	Intermediate Similarity	NPC50443
0.7356	Intermediate Similarity	NPC18536
0.7349	Intermediate Similarity	NPC471037
0.7349	Intermediate Similarity	NPC472847
0.7349	Intermediate Similarity	NPC243347
0.7349	Intermediate Similarity	NPC476721
0.7342	Intermediate Similarity	NPC474020
0.7333	Intermediate Similarity	NPC119838
0.7333	Intermediate Similarity	NPC235109
0.7333	Intermediate Similarity	NPC116683
0.7333	Intermediate Similarity	NPC93245
0.7326	Intermediate Similarity	NPC477128
0.7326	Intermediate Similarity	NPC236459
0.7317	Intermediate Similarity	NPC472229
0.7317	Intermediate Similarity	NPC472230
0.7317	Intermediate Similarity	NPC476071
0.7308	Intermediate Similarity	NPC74639
0.7308	Intermediate Similarity	NPC272359
0.7294	Intermediate Similarity	NPC476717
0.7294	Intermediate Similarity	NPC6979
0.7294	Intermediate Similarity	NPC474008
0.7294	Intermediate Similarity	NPC185638
0.7294	Intermediate Similarity	NPC471042
0.7294	Intermediate Similarity	NPC9231
0.7294	Intermediate Similarity	NPC472272
0.7294	Intermediate Similarity	NPC92139
0.7294	Intermediate Similarity	NPC85698
0.7284	Intermediate Similarity	NPC476176
0.7273	Intermediate Similarity	NPC49420
0.7273	Intermediate Similarity	NPC474065
0.7273	Intermediate Similarity	NPC126642
0.7273	Intermediate Similarity	NPC160506
0.7262	Intermediate Similarity	NPC219011
0.7262	Intermediate Similarity	NPC219535
0.7262	Intermediate Similarity	NPC105895
0.7262	Intermediate Similarity	NPC237938
0.7262	Intermediate Similarity	NPC475509
0.7253	Intermediate Similarity	NPC136781
0.725	Intermediate Similarity	NPC212453
0.725	Intermediate Similarity	NPC477918
0.725	Intermediate Similarity	NPC475031
0.725	Intermediate Similarity	NPC23884
0.725	Intermediate Similarity	NPC474433

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 NPC109510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	3580
0.2-0.3	3495
0.3-0.4	1035
0.4-0.5	289
0.5-0.6	229
0.6-0.7	128
0.7-0.8	19
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7922	Intermediate Similarity	NPD6116	Phase 1
0.7792	Intermediate Similarity	NPD6117	Approved
0.7733	Intermediate Similarity	NPD5777	Approved
0.7595	Intermediate Similarity	NPD6114	Approved
0.7595	Intermediate Similarity	NPD6697	Approved
0.7595	Intermediate Similarity	NPD6118	Approved
0.7595	Intermediate Similarity	NPD6115	Approved
0.7532	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3702	Approved
0.7333	Intermediate Similarity	NPD229	Approved
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7237	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4224	Phase 2
0.7051	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3703	Phase 2
0.6933	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6905	Remote Similarity	NPD1780	Approved
0.6905	Remote Similarity	NPD1779	Approved
0.6883	Remote Similarity	NPD5360	Phase 3
0.6883	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6081	Approved
0.6813	Remote Similarity	NPD6399	Phase 3
0.6795	Remote Similarity	NPD3698	Phase 2
0.6782	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6008	Approved
0.6709	Remote Similarity	NPD4244	Approved
0.6709	Remote Similarity	NPD4245	Approved
0.6702	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4758	Discontinued
0.6591	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD7748	Approved
0.6548	Remote Similarity	NPD3671	Phase 1
0.6517	Remote Similarity	NPD6409	Approved
0.6517	Remote Similarity	NPD5330	Approved
0.6517	Remote Similarity	NPD7334	Approved
0.6517	Remote Similarity	NPD7146	Approved
0.6517	Remote Similarity	NPD7521	Approved
0.6517	Remote Similarity	NPD6684	Approved
0.65	Remote Similarity	NPD4789	Approved
0.6471	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3573	Approved
0.6437	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.6383	Remote Similarity	NPD6001	Approved
0.6375	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3726	Approved
0.6375	Remote Similarity	NPD3725	Approved
0.6374	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6672	Approved
0.6374	Remote Similarity	NPD5737	Approved
0.6374	Remote Similarity	NPD6903	Approved
0.6373	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6373	Approved
0.6373	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD3669	Approved
0.6364	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5364	Discontinued
0.6344	Remote Similarity	NPD7515	Phase 2
0.6337	Remote Similarity	NPD5701	Approved
0.6337	Remote Similarity	NPD5697	Approved
0.6333	Remote Similarity	NPD3618	Phase 1
0.6275	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD6881	Approved
0.6275	Remote Similarity	NPD6899	Approved
0.6275	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD615	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6650	Approved
0.6214	Remote Similarity	NPD6013	Approved
0.6214	Remote Similarity	NPD6014	Approved
0.6214	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6098	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6129	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD5696	Approved
0.6122	Remote Similarity	NPD7638	Approved
0.6122	Remote Similarity	NPD4225	Approved
0.6111	Remote Similarity	NPD3668	Phase 3
0.6105	Remote Similarity	NPD4202	Approved
0.6095	Remote Similarity	NPD6617	Approved
0.6095	Remote Similarity	NPD8130	Phase 1
0.6095	Remote Similarity	NPD6869	Approved
0.6095	Remote Similarity	NPD6847	Approved
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3667	Approved
0.6064	Remote Similarity	NPD5207	Approved
0.6061	Remote Similarity	NPD8418	Phase 2
0.6061	Remote Similarity	NPD7639	Approved
0.6061	Remote Similarity	NPD7640	Approved
0.6058	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3198	Approved
0.6038	Remote Similarity	NPD6882	Approved
0.6038	Remote Similarity	NPD8297	Approved
0.6023	Remote Similarity	NPD6928	Phase 2
0.6022	Remote Similarity	NPD5208	Approved
0.602	Remote Similarity	NPD6084	Phase 2
0.602	Remote Similarity	NPD4755	Approved
0.602	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD5693	Phase 1
0.598	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5695	Phase 3
0.5978	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4802	Phase 2
0.5977	Remote Similarity	NPD4238	Approved
0.5957	Remote Similarity	NPD5328	Approved
0.5941	Remote Similarity	NPD7632	Discontinued
0.5934	Remote Similarity	NPD4786	Approved
0.5918	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4697	Phase 3
0.5904	Remote Similarity	NPD2687	Approved
0.5904	Remote Similarity	NPD2686	Approved
0.5904	Remote Similarity	NPD2254	Approved
0.5904	Remote Similarity	NPD4787	Phase 1
0.59	Remote Similarity	NPD4700	Approved
0.59	Remote Similarity	NPD5285	Approved
0.59	Remote Similarity	NPD4696	Approved
0.59	Remote Similarity	NPD5286	Approved
0.5895	Remote Similarity	NPD5692	Phase 3
0.5893	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2699	Approved
0.5872	Remote Similarity	NPD6274	Approved
0.5862	Remote Similarity	NPD8143	Approved
0.5862	Remote Similarity	NPD8144	Approved
0.5857	Remote Similarity	NPD2266	Phase 2
0.5843	Remote Similarity	NPD7525	Registered
0.5842	Remote Similarity	NPD5223	Approved
0.5833	Remote Similarity	NPD5284	Approved
0.5833	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD5281	Approved
0.5833	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD6079	Approved
0.5833	Remote Similarity	NPD6050	Approved
0.5824	Remote Similarity	NPD4788	Approved
0.5821	Remote Similarity	NPD387	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7115	Discovery
0.5818	Remote Similarity	NPD6317	Approved
0.5789	Remote Similarity	NPD6051	Approved
0.5784	Remote Similarity	NPD4633	Approved
0.5784	Remote Similarity	NPD5224	Approved
0.5784	Remote Similarity	NPD5225	Approved
0.5784	Remote Similarity	NPD5211	Phase 2
0.5784	Remote Similarity	NPD5226	Approved
0.5766	Remote Similarity	NPD6314	Approved
0.5766	Remote Similarity	NPD6313	Approved
0.5766	Remote Similarity	NPD6335	Approved
0.5761	Remote Similarity	NPD3666	Approved
0.5761	Remote Similarity	NPD3133	Approved
0.5761	Remote Similarity	NPD3665	Phase 1
0.5758	Remote Similarity	NPD5222	Approved
0.5758	Remote Similarity	NPD5221	Approved
0.5758	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6921	Approved
0.575	Remote Similarity	NPD7909	Approved
0.575	Remote Similarity	NPD371	Approved
0.5728	Remote Similarity	NPD5174	Approved
0.5728	Remote Similarity	NPD4754	Approved
0.5728	Remote Similarity	NPD5175	Approved
0.5728	Remote Similarity	NPD6052	Approved
0.5714	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD7100	Approved
0.57	Remote Similarity	NPD5173	Approved
0.5676	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6009	Approved
0.5673	Remote Similarity	NPD5141	Approved
0.567	Remote Similarity	NPD6411	Approved
0.5664	Remote Similarity	NPD6319	Approved
0.5657	Remote Similarity	NPD5654	Approved
0.5634	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD2257	Approved
0.5625	Remote Similarity	NPD4753	Phase 2
0.5619	Remote Similarity	NPD4768	Approved
0.5619	Remote Similarity	NPD4767	Approved
0.5619	Remote Similarity	NPD6920	Discontinued
0.5618	Remote Similarity	NPD3617	Approved
0.5614	Remote Similarity	NPD5983	Phase 2
0.5614	Remote Similarity	NPD6909	Approved
0.5614	Remote Similarity	NPD6908	Approved
0.5603	Remote Similarity	NPD7492	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