NPASS Compound

Structure

NPC71541 OpenBabel07101718292D 30 33 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 3.8415 0.2751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8735 -3.1336 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 -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 0.1691 -1.6092 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 1.1691 0.1229 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 2.1473 -0.0850 0.0000 C 0 0 2 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 1.3383 -1.4863 0.0000 C 0 0 2 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 0.6691 -0.7431 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 2.8904 0.5841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1303 -2.4644 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 2.2518 -1.0796 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 1 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 6 0 0 0 18 26 1 6 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 6 0 0 0 20 23 1 1 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 22 24 1 1 0 0 0 23 11 1 6 0 0 0 23 30 1 0 0 0 0 24 12 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.28
Volume:	439.539
LogP:	4.36
LogD:	3.777
LogS:	-4.869
# Rotatable Bonds:	4
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	5.825
Fsp3:	0.958
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.845
MDCK Permeability:	2.04940079129301e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.213

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	87.48429107666016%
Volume Distribution (VD):	2.043
Pgp-substrate:	8.471779823303223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.223
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	8.036
Half-life (T1/2):	0.225

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.774
Drug-inuced Liver Injury (DILI):	0.639
AMES Toxicity:	0.974
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.452
Skin Sensitization:	0.76
Carcinogencity:	0.689
Eye Corrosion:	0.012
Eye Irritation:	0.063
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC71541

Natural Product ID:	NPC71541
*Common Name:**	YCGYYZXBHVNOIX-VBKRYCECSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YCGYYZXBHVNOIX-VBKRYCECSA-N
Standard InCHI:	InChI=1S/C24H40O6/c1-15-13-17(28-16(2)25)19-21(3,4)9-8-10-22(19,5)24(15)12-11-23(30-24)14-18(26-6)29-20(23)27-7/h15,17-20H,8-14H2,1-7H3/t15-,17-,18-,19+,20-,22+,23+,24-/m1/s1
SMILES:	C[C@@H]1C[C@H]([C@H]2C(C)(C)CCC[C@]2(C)[C@]21CC[C@@]1(C[C@H](OC)O[C@H]1OC)O2)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517633
PubChem CID:	11796606
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
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[480101]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	>	5.0	ug.mL-1	PMID[480101]

☑ 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 NPC71541 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	431
0.1-0.2	4342
0.2-0.3	13045
0.3-0.4	10759
0.4-0.5	5941
0.5-0.6	5670
0.6-0.7	2110
0.7-0.8	363
0.8-0.85	21
0.85-0.9	7
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC471216
0.9867	High Similarity	NPC471217
0.9136	High Similarity	NPC474008
0.9125	High Similarity	NPC18953
0.9024	High Similarity	NPC110365
0.9024	High Similarity	NPC45833
0.9024	High Similarity	NPC213658
0.9024	High Similarity	NPC62202
0.8916	High Similarity	NPC470872
0.8916	High Similarity	NPC221993
0.8902	High Similarity	NPC471410
0.8902	High Similarity	NPC471411
0.878	High Similarity	NPC235402
0.8625	High Similarity	NPC475456
0.8506	High Similarity	NPC35164
0.8506	High Similarity	NPC475307
0.8434	Intermediate Similarity	NPC65133
0.8354	Intermediate Similarity	NPC107963
0.8333	Intermediate Similarity	NPC266417
0.8315	Intermediate Similarity	NPC21897
0.8313	Intermediate Similarity	NPC474284
0.8313	Intermediate Similarity	NPC474346
0.8313	Intermediate Similarity	NPC474253
0.8313	Intermediate Similarity	NPC475820
0.8313	Intermediate Similarity	NPC213737
0.8293	Intermediate Similarity	NPC470154
0.8272	Intermediate Similarity	NPC477287
0.8222	Intermediate Similarity	NPC145553
0.8205	Intermediate Similarity	NPC123122
0.8193	Intermediate Similarity	NPC208912
0.8193	Intermediate Similarity	NPC2096
0.8193	Intermediate Similarity	NPC477447
0.8193	Intermediate Similarity	NPC477284
0.8193	Intermediate Similarity	NPC477446
0.8193	Intermediate Similarity	NPC470155
0.8171	Intermediate Similarity	NPC472951
0.8171	Intermediate Similarity	NPC472943
0.809	Intermediate Similarity	NPC122083
0.809	Intermediate Similarity	NPC182740
0.809	Intermediate Similarity	NPC256104
0.809	Intermediate Similarity	NPC211845
0.8072	Intermediate Similarity	NPC470156
0.8046	Intermediate Similarity	NPC471221
0.8043	Intermediate Similarity	NPC292775
0.8023	Intermediate Similarity	NPC268633
0.8022	Intermediate Similarity	NPC238796
0.8022	Intermediate Similarity	NPC237071
0.8022	Intermediate Similarity	NPC203434
0.8022	Intermediate Similarity	NPC475765
0.8022	Intermediate Similarity	NPC475785
0.7978	Intermediate Similarity	NPC475878
0.7975	Intermediate Similarity	NPC476718
0.7952	Intermediate Similarity	NPC134227
0.7935	Intermediate Similarity	NPC113976
0.7935	Intermediate Similarity	NPC198549
0.7927	Intermediate Similarity	NPC177343
0.7927	Intermediate Similarity	NPC272841
0.7889	Intermediate Similarity	NPC12297
0.7882	Intermediate Similarity	NPC241959
0.7849	Intermediate Similarity	NPC471375
0.7849	Intermediate Similarity	NPC209798
0.7849	Intermediate Similarity	NPC471374
0.7816	Intermediate Similarity	NPC477283
0.7816	Intermediate Similarity	NPC107603
0.7816	Intermediate Similarity	NPC215968
0.7816	Intermediate Similarity	NPC155531
0.7802	Intermediate Similarity	NPC151214
0.7802	Intermediate Similarity	NPC191915
0.7791	Intermediate Similarity	NPC471367
0.7766	Intermediate Similarity	NPC471428
0.7766	Intermediate Similarity	NPC51579
0.7766	Intermediate Similarity	NPC470030
0.7766	Intermediate Similarity	NPC471426
0.7766	Intermediate Similarity	NPC471427
0.7765	Intermediate Similarity	NPC286719
0.7765	Intermediate Similarity	NPC477286
0.7753	Intermediate Similarity	NPC82955
0.7738	Intermediate Similarity	NPC186588
0.7727	Intermediate Similarity	NPC161928
0.7727	Intermediate Similarity	NPC210658
0.7717	Intermediate Similarity	NPC57964
0.7717	Intermediate Similarity	NPC94582
0.7701	Intermediate Similarity	NPC290612
0.7684	Intermediate Similarity	NPC472081
0.7684	Intermediate Similarity	NPC108227
0.7684	Intermediate Similarity	NPC475574
0.7684	Intermediate Similarity	NPC476512
0.7683	Intermediate Similarity	NPC136424
0.7674	Intermediate Similarity	NPC111582
0.7674	Intermediate Similarity	NPC477285
0.7654	Intermediate Similarity	NPC308489
0.7654	Intermediate Similarity	NPC55508
0.7647	Intermediate Similarity	NPC190940
0.764	Intermediate Similarity	NPC128475
0.764	Intermediate Similarity	NPC476435
0.7634	Intermediate Similarity	NPC156377
0.7634	Intermediate Similarity	NPC252056
0.7619	Intermediate Similarity	NPC474754
0.7614	Intermediate Similarity	NPC471369
0.7604	Intermediate Similarity	NPC470029
0.7604	Intermediate Similarity	NPC310138
0.7604	Intermediate Similarity	NPC134967
0.7604	Intermediate Similarity	NPC114700
0.759	Intermediate Similarity	NPC476719
0.7582	Intermediate Similarity	NPC210759
0.7582	Intermediate Similarity	NPC59006
0.7582	Intermediate Similarity	NPC307167
0.7582	Intermediate Similarity	NPC229801
0.7561	Intermediate Similarity	NPC472950
0.7561	Intermediate Similarity	NPC472952
0.7558	Intermediate Similarity	NPC470611
0.7556	Intermediate Similarity	NPC20822
0.7531	Intermediate Similarity	NPC109510
0.7529	Intermediate Similarity	NPC474714
0.7529	Intermediate Similarity	NPC125366
0.7529	Intermediate Similarity	NPC60568
0.7528	Intermediate Similarity	NPC140446
0.7528	Intermediate Similarity	NPC43912
0.7528	Intermediate Similarity	NPC472396
0.7526	Intermediate Similarity	NPC97260
0.7526	Intermediate Similarity	NPC476837
0.7526	Intermediate Similarity	NPC139181
0.75	Intermediate Similarity	NPC475767
0.75	Intermediate Similarity	NPC470623
0.75	Intermediate Similarity	NPC252483
0.75	Intermediate Similarity	NPC43463
0.75	Intermediate Similarity	NPC119467
0.75	Intermediate Similarity	NPC18724
0.75	Intermediate Similarity	NPC167644
0.75	Intermediate Similarity	NPC323231
0.75	Intermediate Similarity	NPC311246
0.75	Intermediate Similarity	NPC171741
0.75	Intermediate Similarity	NPC224003
0.75	Intermediate Similarity	NPC191345
0.7473	Intermediate Similarity	NPC473542
0.7473	Intermediate Similarity	NPC470114
0.7471	Intermediate Similarity	NPC470070
0.7467	Intermediate Similarity	NPC204173
0.7449	Intermediate Similarity	NPC470043
0.7449	Intermediate Similarity	NPC470060
0.7449	Intermediate Similarity	NPC470059
0.7449	Intermediate Similarity	NPC470062
0.7449	Intermediate Similarity	NPC470058
0.7449	Intermediate Similarity	NPC470057
0.7449	Intermediate Similarity	NPC470061
0.7449	Intermediate Similarity	NPC85593
0.7449	Intermediate Similarity	NPC470064
0.7449	Intermediate Similarity	NPC31430
0.7447	Intermediate Similarity	NPC296936
0.7444	Intermediate Similarity	NPC201607
0.7444	Intermediate Similarity	NPC56777
0.7444	Intermediate Similarity	NPC263079
0.7442	Intermediate Similarity	NPC476494
0.7439	Intermediate Similarity	NPC470151
0.7423	Intermediate Similarity	NPC213528
0.7423	Intermediate Similarity	NPC244969
0.7419	Intermediate Similarity	NPC3538
0.7419	Intermediate Similarity	NPC471373
0.7419	Intermediate Similarity	NPC253611
0.7419	Intermediate Similarity	NPC113500
0.7419	Intermediate Similarity	NPC477224
0.7419	Intermediate Similarity	NPC175
0.7419	Intermediate Similarity	NPC267238
0.7419	Intermediate Similarity	NPC252253
0.7419	Intermediate Similarity	NPC45959
0.7419	Intermediate Similarity	NPC148593
0.7419	Intermediate Similarity	NPC305418
0.7419	Intermediate Similarity	NPC30687
0.7419	Intermediate Similarity	NPC77717
0.7416	Intermediate Similarity	NPC477441
0.7416	Intermediate Similarity	NPC114378
0.7416	Intermediate Similarity	NPC471368
0.7416	Intermediate Similarity	NPC131365
0.7416	Intermediate Similarity	NPC103782
0.7412	Intermediate Similarity	NPC476176
0.7391	Intermediate Similarity	NPC473066
0.7391	Intermediate Similarity	NPC149966
0.7391	Intermediate Similarity	NPC216137
0.7391	Intermediate Similarity	NPC5632
0.7386	Intermediate Similarity	NPC474156
0.7386	Intermediate Similarity	NPC79308
0.7374	Intermediate Similarity	NPC291414
0.7368	Intermediate Similarity	NPC470591
0.7368	Intermediate Similarity	NPC472273
0.7363	Intermediate Similarity	NPC131466
0.7356	Intermediate Similarity	NPC154043
0.7356	Intermediate Similarity	NPC202688
0.7356	Intermediate Similarity	NPC216800
0.7356	Intermediate Similarity	NPC60018
0.7349	Intermediate Similarity	NPC186851
0.7342	Intermediate Similarity	NPC476928
0.734	Intermediate Similarity	NPC471429
0.734	Intermediate Similarity	NPC473064
0.734	Intermediate Similarity	NPC473065
0.734	Intermediate Similarity	NPC471424
0.734	Intermediate Similarity	NPC189575
0.734	Intermediate Similarity	NPC471425
0.734	Intermediate Similarity	NPC106701
0.734	Intermediate Similarity	NPC473067
0.734	Intermediate Similarity	NPC205129

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 NPC71541 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	4329
0.2-0.3	3073
0.3-0.4	723
0.4-0.5	336
0.5-0.6	209
0.6-0.7	52
0.7-0.8	1
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
0.7284	Intermediate Similarity	NPD2686	Approved
0.7284	Intermediate Similarity	NPD2254	Approved
0.7284	Intermediate Similarity	NPD2687	Approved
0.7128	Intermediate Similarity	NPD8171	Discontinued
0.7079	Intermediate Similarity	NPD3669	Approved
0.7079	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1780	Approved
0.7045	Intermediate Similarity	NPD1779	Approved
0.6932	Remote Similarity	NPD6928	Phase 2
0.6867	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1810	Approved
0.6824	Remote Similarity	NPD1811	Approved
0.6765	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7327	Approved
0.6636	Remote Similarity	NPD7328	Approved
0.6577	Remote Similarity	NPD7516	Approved
0.6517	Remote Similarity	NPD6697	Approved
0.6517	Remote Similarity	NPD6114	Approved
0.6517	Remote Similarity	NPD6118	Approved
0.6517	Remote Similarity	NPD6115	Approved
0.6509	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1700	Approved
0.6422	Remote Similarity	NPD8133	Approved
0.6404	Remote Similarity	NPD6116	Phase 1
0.6372	Remote Similarity	NPD8377	Approved
0.6372	Remote Similarity	NPD8294	Approved
0.6353	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8380	Approved
0.6316	Remote Similarity	NPD8296	Approved
0.6316	Remote Similarity	NPD8033	Approved
0.6316	Remote Similarity	NPD8335	Approved
0.6316	Remote Similarity	NPD8379	Approved
0.6316	Remote Similarity	NPD8378	Approved
0.6292	Remote Similarity	NPD6117	Approved
0.6207	Remote Similarity	NPD5777	Approved
0.6186	Remote Similarity	NPD8293	Discontinued
0.6168	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6940	Discontinued
0.6145	Remote Similarity	NPD371	Approved
0.6139	Remote Similarity	NPD7991	Discontinued
0.6134	Remote Similarity	NPD7736	Approved
0.6121	Remote Similarity	NPD6370	Approved
0.6111	Remote Similarity	NPD6686	Approved
0.6111	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7507	Approved
0.6067	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD229	Approved
0.6034	Remote Similarity	NPD7503	Approved
0.6019	Remote Similarity	NPD6412	Phase 2
0.6017	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6616	Approved
0.595	Remote Similarity	NPD7319	Approved
0.5948	Remote Similarity	NPD6054	Approved
0.5948	Remote Similarity	NPD6059	Approved
0.5926	Remote Similarity	NPD6008	Approved
0.5917	Remote Similarity	NPD7078	Approved
0.5875	Remote Similarity	NPD2267	Suspended
0.5842	Remote Similarity	NPD8035	Phase 2
0.5842	Remote Similarity	NPD8034	Phase 2
0.5833	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3702	Approved
0.5824	Remote Similarity	NPD3703	Phase 2
0.581	Remote Similarity	NPD7638	Approved
0.5798	Remote Similarity	NPD6067	Discontinued
0.5798	Remote Similarity	NPD8328	Phase 3
0.5783	Remote Similarity	NPD1145	Discontinued
0.5763	Remote Similarity	NPD6016	Approved
0.5763	Remote Similarity	NPD6015	Approved
0.5755	Remote Similarity	NPD7640	Approved
0.5755	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD5988	Approved
0.5698	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6009	Approved
0.5667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4225	Approved
0.5648	Remote Similarity	NPD7632	Discontinued
0.5618	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6882	Approved
0.5607	Remote Similarity	NPD6648	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