NPASS Compound

Structure

NPC471411 OpenBabel07101718182D 30 33 0 0 1 0 0 0 0 0999 V2000 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 23 1 1 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 6 0 0 0 16 20 1 0 0 0 0 16 21 1 6 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 17 25 1 0 0 0 0 18 27 1 6 0 0 0 18 29 1 0 0 0 0 19 22 1 6 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 21 23 1 1 0 0 0 22 26 1 6 0 0 0 23 11 1 6 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.26
Volume:	431.033
LogP:	3.669
LogD:	3.212
LogS:	-4.321
# Rotatable Bonds:	3
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.656
Synthetic Accessibility Score:	5.636
Fsp3:	0.957
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:	-4.733
MDCK Permeability:	1.857400820881594e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.397

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	84.45438385009766%
Volume Distribution (VD):	1.533
Pgp-substrate:	20.240699768066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.891
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	2.63
Half-life (T1/2):	0.403

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.526
Carcinogencity:	0.471
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC471411

Natural Product ID:	NPC471411
*Common Name:**	Viteagnusin G
IUPAC Name:	[(1R,2'R,3R,3'S,3'aR,4R,4aS,7'aS,8aS)-3',3'a-dihydroxy-2'-methoxy-3,4a,8,8-tetramethylspiro[2,3,5,6,7,8a-hexahydro-1H-naphthalene-4,6'-3,4,5,7a-tetrahydro-2H-furo[2,3-b]pyran]-1-yl] acetate
Synonyms:
Standard InCHIKey:	GSXSRLNHVCOZGT-BETHHPKWSA-N
Standard InCHI:	InChI=1S/C23H38O7/c1-13-12-15(28-14(2)24)16-20(3,4)8-7-9-21(16,5)23(13)11-10-22(26)17(25)18(27-6)29-19(22)30-23/h13,15-19,25-26H,7-12H2,1-6H3/t13-,15-,16+,17-,18-,19-,21+,22-,23-/m1/s1
SMILES:	CO[C@@H]1O[C@H]2[C@@]([C@@H]1O)(O)CC[C@@]1(O2)[C@H](C)C[C@H]([C@@H]2[C@]1(C)CCCC2(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436609
PubChem CID:	44475044
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
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[490876]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	29300.0	nM	PMID[490876]

☑ 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 NPC471411 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	414
0.1-0.2	3465
0.2-0.3	10352
0.3-0.4	12431
0.4-0.5	6187
0.5-0.6	4643
0.6-0.7	3775
0.7-0.8	1275
0.8-0.85	112
0.85-0.9	41
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471410
0.9268	High Similarity	NPC18953
0.9167	High Similarity	NPC213658
0.9167	High Similarity	NPC62202
0.9167	High Similarity	NPC110365
0.9167	High Similarity	NPC45833
0.9	High Similarity	NPC177343
0.8916	High Similarity	NPC241959
0.8916	High Similarity	NPC474253
0.8916	High Similarity	NPC475820
0.8916	High Similarity	NPC474346
0.8916	High Similarity	NPC213737
0.8916	High Similarity	NPC474284
0.8902	High Similarity	NPC71541
0.8837	High Similarity	NPC470872
0.8795	High Similarity	NPC470155
0.8795	High Similarity	NPC477446
0.8795	High Similarity	NPC477447
0.8795	High Similarity	NPC2096
0.8795	High Similarity	NPC208912
0.8791	High Similarity	NPC471374
0.8791	High Similarity	NPC209798
0.8791	High Similarity	NPC471375
0.878	High Similarity	NPC472943
0.878	High Similarity	NPC472951
0.878	High Similarity	NPC471216
0.878	High Similarity	NPC471217
0.8778	High Similarity	NPC238796
0.8778	High Similarity	NPC203434
0.8778	High Similarity	NPC237071
0.8765	High Similarity	NPC272841
0.8764	High Similarity	NPC151214
0.8764	High Similarity	NPC191915
0.8706	High Similarity	NPC235402
0.8706	High Similarity	NPC290612
0.8696	High Similarity	NPC471426
0.8696	High Similarity	NPC471428
0.8696	High Similarity	NPC471427
0.8696	High Similarity	NPC51579
0.8675	High Similarity	NPC470156
0.8675	High Similarity	NPC470154
0.8667	High Similarity	NPC94582
0.8667	High Similarity	NPC57964
0.8652	High Similarity	NPC475307
0.8571	High Similarity	NPC252056
0.8523	High Similarity	NPC82955
0.8506	High Similarity	NPC43912
0.8506	High Similarity	NPC140446
0.85	High Similarity	NPC308489
0.8495	Intermediate Similarity	NPC470030
0.8462	Intermediate Similarity	NPC21897
0.8444	Intermediate Similarity	NPC323231
0.8444	Intermediate Similarity	NPC224003
0.8444	Intermediate Similarity	NPC182740
0.8444	Intermediate Similarity	NPC211845
0.8444	Intermediate Similarity	NPC171741
0.8444	Intermediate Similarity	NPC256104
0.8444	Intermediate Similarity	NPC470623
0.8444	Intermediate Similarity	NPC122083
0.8444	Intermediate Similarity	NPC18724
0.8404	Intermediate Similarity	NPC475574
0.8404	Intermediate Similarity	NPC472081
0.8404	Intermediate Similarity	NPC476512
0.8404	Intermediate Similarity	NPC108227
0.8391	Intermediate Similarity	NPC215968
0.8391	Intermediate Similarity	NPC155531
0.8391	Intermediate Similarity	NPC268633
0.837	Intermediate Similarity	NPC296936
0.837	Intermediate Similarity	NPC475785
0.837	Intermediate Similarity	NPC156377
0.8352	Intermediate Similarity	NPC471373
0.8352	Intermediate Similarity	NPC77717
0.8352	Intermediate Similarity	NPC148593
0.8352	Intermediate Similarity	NPC267238
0.8352	Intermediate Similarity	NPC253611
0.8333	Intermediate Similarity	NPC186588
0.8333	Intermediate Similarity	NPC229801
0.8333	Intermediate Similarity	NPC307167
0.8333	Intermediate Similarity	NPC210759
0.8333	Intermediate Similarity	NPC475456
0.8316	Intermediate Similarity	NPC470029
0.8316	Intermediate Similarity	NPC114700
0.8316	Intermediate Similarity	NPC134967
0.8316	Intermediate Similarity	NPC310138
0.8315	Intermediate Similarity	NPC131466
0.8293	Intermediate Similarity	NPC136424
0.8293	Intermediate Similarity	NPC107963
0.828	Intermediate Similarity	NPC472273
0.828	Intermediate Similarity	NPC470591
0.8261	Intermediate Similarity	NPC189575
0.8261	Intermediate Similarity	NPC106701
0.8261	Intermediate Similarity	NPC471429
0.8261	Intermediate Similarity	NPC471425
0.8261	Intermediate Similarity	NPC471424
0.8261	Intermediate Similarity	NPC205129
0.8256	Intermediate Similarity	NPC477285
0.8256	Intermediate Similarity	NPC111582
0.8242	Intermediate Similarity	NPC311246
0.8242	Intermediate Similarity	NPC167644
0.8229	Intermediate Similarity	NPC97260
0.8229	Intermediate Similarity	NPC476837
0.8229	Intermediate Similarity	NPC139181
0.8222	Intermediate Similarity	NPC279329
0.8222	Intermediate Similarity	NPC473542
0.8211	Intermediate Similarity	NPC476839
0.8211	Intermediate Similarity	NPC476838
0.8202	Intermediate Similarity	NPC281004
0.8191	Intermediate Similarity	NPC292775
0.8182	Intermediate Similarity	NPC474008
0.8182	Intermediate Similarity	NPC477283
0.8182	Intermediate Similarity	NPC107603
0.8172	Intermediate Similarity	NPC475765
0.8171	Intermediate Similarity	NPC472952
0.8171	Intermediate Similarity	NPC472950
0.8163	Intermediate Similarity	NPC126753
0.8161	Intermediate Similarity	NPC474156
0.8152	Intermediate Similarity	NPC211238
0.8152	Intermediate Similarity	NPC113500
0.8152	Intermediate Similarity	NPC45959
0.8152	Intermediate Similarity	NPC175
0.8152	Intermediate Similarity	NPC30687
0.8152	Intermediate Similarity	NPC477224
0.8152	Intermediate Similarity	NPC252253
0.8152	Intermediate Similarity	NPC3538
0.8152	Intermediate Similarity	NPC305418
0.814	Intermediate Similarity	NPC477286
0.814	Intermediate Similarity	NPC154043
0.814	Intermediate Similarity	NPC286719
0.814	Intermediate Similarity	NPC202688
0.814	Intermediate Similarity	NPC60018
0.8132	Intermediate Similarity	NPC36372
0.8132	Intermediate Similarity	NPC475878
0.8132	Intermediate Similarity	NPC293609
0.8132	Intermediate Similarity	NPC149966
0.8132	Intermediate Similarity	NPC59006
0.8132	Intermediate Similarity	NPC5632
0.8111	Intermediate Similarity	NPC102725
0.8111	Intermediate Similarity	NPC20822
0.8111	Intermediate Similarity	NPC473472
0.8105	Intermediate Similarity	NPC317019
0.8095	Intermediate Similarity	NPC43463
0.8095	Intermediate Similarity	NPC191345
0.8095	Intermediate Similarity	NPC252483
0.809	Intermediate Similarity	NPC210658
0.809	Intermediate Similarity	NPC161928
0.809	Intermediate Similarity	NPC472396
0.8085	Intermediate Similarity	NPC210157
0.8085	Intermediate Similarity	NPC473555
0.8085	Intermediate Similarity	NPC278939
0.8085	Intermediate Similarity	NPC471770
0.8081	Intermediate Similarity	NPC207693
0.8068	Intermediate Similarity	NPC266651
0.8065	Intermediate Similarity	NPC215570
0.8065	Intermediate Similarity	NPC473064
0.8065	Intermediate Similarity	NPC473065
0.8065	Intermediate Similarity	NPC477494
0.8065	Intermediate Similarity	NPC473067
0.8049	Intermediate Similarity	NPC166250
0.8049	Intermediate Similarity	NPC470151
0.8046	Intermediate Similarity	NPC470070
0.8043	Intermediate Similarity	NPC88962
0.8043	Intermediate Similarity	NPC277774
0.8043	Intermediate Similarity	NPC144790
0.8043	Intermediate Similarity	NPC149400
0.8023	Intermediate Similarity	NPC190940
0.8022	Intermediate Similarity	NPC50443
0.8022	Intermediate Similarity	NPC261990
0.8022	Intermediate Similarity	NPC65550
0.8022	Intermediate Similarity	NPC223143
0.8022	Intermediate Similarity	NPC474249
0.8022	Intermediate Similarity	NPC18536
0.8	Intermediate Similarity	NPC476379
0.8	Intermediate Similarity	NPC128475
0.8	Intermediate Similarity	NPC22709
0.8	Intermediate Similarity	NPC221993
0.8	Intermediate Similarity	NPC471221
0.8	Intermediate Similarity	NPC157739
0.7979	Intermediate Similarity	NPC476510
0.7979	Intermediate Similarity	NPC142264
0.7979	Intermediate Similarity	NPC139271
0.7979	Intermediate Similarity	NPC304011
0.7978	Intermediate Similarity	NPC471240
0.7976	Intermediate Similarity	NPC476719
0.7959	Intermediate Similarity	NPC470043
0.7959	Intermediate Similarity	NPC85593
0.7959	Intermediate Similarity	NPC470062
0.7959	Intermediate Similarity	NPC470059
0.7959	Intermediate Similarity	NPC470064
0.7959	Intermediate Similarity	NPC470058
0.7959	Intermediate Similarity	NPC470060
0.7959	Intermediate Similarity	NPC470061
0.7959	Intermediate Similarity	NPC31430
0.7959	Intermediate Similarity	NPC470057
0.7957	Intermediate Similarity	NPC312678
0.7957	Intermediate Similarity	NPC96736
0.7957	Intermediate Similarity	NPC473851
0.7957	Intermediate Similarity	NPC178949
0.7957	Intermediate Similarity	NPC253268
0.7957	Intermediate Similarity	NPC24960
0.7957	Intermediate Similarity	NPC131693

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 NPC471411 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	3743
0.2-0.3	3345
0.3-0.4	932
0.4-0.5	347
0.5-0.6	271
0.6-0.7	71
0.7-0.8	25
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
0.7849	Intermediate Similarity	NPD8171	Discontinued
0.764	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3669	Approved
0.7619	Intermediate Similarity	NPD1810	Approved
0.7619	Intermediate Similarity	NPD1811	Approved
0.75	Intermediate Similarity	NPD6928	Phase 2
0.747	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2254	Approved
0.7262	Intermediate Similarity	NPD2687	Approved
0.7262	Intermediate Similarity	NPD2686	Approved
0.7248	Intermediate Similarity	NPD7327	Approved
0.7248	Intermediate Similarity	NPD7328	Approved
0.7196	Intermediate Similarity	NPD8133	Approved
0.7182	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6118	Approved
0.7079	Intermediate Similarity	NPD6114	Approved
0.7079	Intermediate Similarity	NPD6697	Approved
0.7079	Intermediate Similarity	NPD6115	Approved
0.7033	Intermediate Similarity	NPD1780	Approved
0.7033	Intermediate Similarity	NPD1779	Approved
0.6966	Remote Similarity	NPD6116	Phase 1
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6951	Remote Similarity	NPD371	Approved
0.6909	Remote Similarity	NPD6940	Discontinued
0.6903	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.6903	Remote Similarity	NPD8335	Approved
0.6903	Remote Similarity	NPD8380	Approved
0.6903	Remote Similarity	NPD8296	Approved
0.6903	Remote Similarity	NPD8379	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6686	Approved
0.6854	Remote Similarity	NPD6117	Approved
0.6847	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6412	Phase 2
0.6754	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6629	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7319	Approved
0.6496	Remote Similarity	NPD8328	Phase 3
0.6471	Remote Similarity	NPD8293	Discontinued
0.6471	Remote Similarity	NPD7991	Discontinued
0.6417	Remote Similarity	NPD7736	Approved
0.641	Remote Similarity	NPD6370	Approved
0.6374	Remote Similarity	NPD3702	Approved
0.6374	Remote Similarity	NPD3703	Phase 2
0.6321	Remote Similarity	NPD1700	Approved
0.6306	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7492	Approved
0.6286	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD6059	Approved
0.6239	Remote Similarity	NPD6054	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD7640	Approved
0.6222	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7078	Approved
0.6186	Remote Similarity	NPD6921	Approved
0.618	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD4225	Approved
0.6121	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD4787	Phase 1
0.6098	Remote Similarity	NPD2267	Suspended
0.6083	Remote Similarity	NPD6067	Discontinued
0.6061	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6882	Approved
0.605	Remote Similarity	NPD8516	Approved
0.605	Remote Similarity	NPD8515	Approved
0.605	Remote Similarity	NPD6016	Approved
0.605	Remote Similarity	NPD8517	Approved
0.605	Remote Similarity	NPD6015	Approved
0.605	Remote Similarity	NPD8513	Phase 3
0.6044	Remote Similarity	NPD5777	Approved
0.6042	Remote Similarity	NPD7525	Registered
0.6036	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5988	Approved
0.5982	Remote Similarity	NPD8174	Phase 2
0.5966	Remote Similarity	NPD6319	Approved
0.5963	Remote Similarity	NPD8084	Approved
0.5963	Remote Similarity	NPD8138	Approved
0.5963	Remote Similarity	NPD8086	Approved
0.5963	Remote Similarity	NPD8139	Approved
0.5963	Remote Similarity	NPD8083	Approved
0.5963	Remote Similarity	NPD8082	Approved
0.5963	Remote Similarity	NPD8085	Approved
0.5946	Remote Similarity	NPD6402	Approved
0.5946	Remote Similarity	NPD6675	Approved
0.5946	Remote Similarity	NPD5739	Approved
0.5946	Remote Similarity	NPD7128	Approved
0.5934	Remote Similarity	NPD4245	Approved
0.5934	Remote Similarity	NPD4244	Approved
0.5926	Remote Similarity	NPD887	Approved
0.5926	Remote Similarity	NPD889	Approved
0.5926	Remote Similarity	NPD894	Approved
0.5926	Remote Similarity	NPD895	Approved
0.5913	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD8276	Approved
0.5909	Remote Similarity	NPD8275	Approved
0.5889	Remote Similarity	NPD5360	Phase 3
0.5889	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6081	Approved
0.5856	Remote Similarity	NPD8081	Approved
0.5843	Remote Similarity	NPD4224	Phase 2
0.5841	Remote Similarity	NPD6881	Approved
0.5841	Remote Similarity	NPD7320	Approved
0.5841	Remote Similarity	NPD6899	Approved
0.5824	Remote Similarity	NPD3698	Phase 2
0.5814	Remote Similarity	NPD6123	Approved
0.581	Remote Similarity	NPD6399	Phase 3
0.5804	Remote Similarity	NPD8393	Approved
0.5802	Remote Similarity	NPD2269	Approved
0.5789	Remote Similarity	NPD6372	Approved
0.5789	Remote Similarity	NPD6373	Approved
0.5784	Remote Similarity	NPD7524	Approved
0.578	Remote Similarity	NPD8418	Phase 2
0.5773	Remote Similarity	NPD7645	Phase 2
0.5761	Remote Similarity	NPD4789	Approved
0.576	Remote Similarity	NPD6033	Approved
0.5755	Remote Similarity	NPD7748	Approved
0.5752	Remote Similarity	NPD8140	Approved
0.5752	Remote Similarity	NPD8307	Discontinued
0.5752	Remote Similarity	NPD5697	Approved
0.5752	Remote Similarity	NPD5701	Approved
0.5741	Remote Similarity	NPD7902	Approved
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD7102	Approved
0.5732	Remote Similarity	NPD892	Phase 3
0.5732	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD888	Phase 3
0.5732	Remote Similarity	NPD893	Approved
0.5732	Remote Similarity	NPD891	Phase 3
0.573	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD7515	Phase 2
0.5691	Remote Similarity	NPD7604	Phase 2
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD6617	Approved
0.569	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6649	Approved
0.5679	Remote Similarity	NPD905	Approved
0.5679	Remote Similarity	NPD904	Phase 3
0.567	Remote Similarity	NPD3671	Phase 1
0.567	Remote Similarity	NPD4238	Approved
0.567	Remote Similarity	NPD4802	Phase 2
0.5664	Remote Similarity	NPD6008	Approved
0.5656	Remote Similarity	NPD5983	Phase 2
0.5652	Remote Similarity	NPD8306	Approved
0.5652	Remote Similarity	NPD6013	Approved
0.5652	Remote Similarity	NPD6012	Approved
0.5652	Remote Similarity	NPD6014	Approved
0.5652	Remote Similarity	NPD8305	Approved
0.5644	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6648	Approved
0.562	Remote Similarity	NPD7625	Phase 1
0.5619	Remote Similarity	NPD3168	Discontinued
0.5612	Remote Similarity	NPD7329	Approved
0.5603	Remote Similarity	NPD8087	Discontinued
0.56	Remote Similarity	NPD6336	Discontinued

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