NPASS Compound

Structure

CID20946 OpenBabel06191715342D 26 27 0 0 1 0 0 0 0 0999 V2000 -1.7424 -5.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -4.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 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 0.4483 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 -3.9319 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 -3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 26 1 1 0 0 0 21 25 1 0 0 0 0 22 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.31
Volume:	612.648
LogP:	0.706
LogD:	1.025
LogS:	-2.471
# Rotatable Bonds:	23
TPSA:	202.52
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	1
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.083
Synthetic Accessibility Score:	4.112
Fsp3:	0.655
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.049
MDCK Permeability:	4.6715525968465954e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.727
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	66.81844329833984%
Volume Distribution (VD):	0.363
Pgp-substrate:	43.799461364746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.114
CYP2C9-substrate:	0.761
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	1.737
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.709
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.059
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC20946

Natural Product ID:	NPC20946
*Common Name:**	Vitetrifolin E
IUPAC Name:	[(1S,2R,3S,4R)-2-hydroxy-4-(3-hydroxy-3-methylpent-4-enyl)-3,4,8,8-tetramethyl-1,2,3,5,6,7-hexahydronaphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	HEUKTFJGHNRGIR-VVPBWZQQSA-N
Standard InCHI:	InChI=1S/C22H36O4/c1-8-21(6,25)12-13-22(7)14(2)18(24)19(26-15(3)23)17-16(22)10-9-11-20(17,4)5/h8,14,18-19,24-25H,1,9-13H2,2-7H3/t14-,18-,19+,21?,22-/m1/s1
SMILES:	C=CC(CC[C@]1(C)[C@H](C)[C@@H](O)[C@H](C2=C1CCCC2(C)C)OC(=O)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436601
PubChem CID:	11143042
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	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]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21373	Vitex trifolia	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[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21373	Vitex trifolia	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[496526]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[496526]

☑ 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 NPC20946 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	185
0.1-0.2	1231
0.2-0.3	4484
0.3-0.4	12917
0.4-0.5	11603
0.5-0.6	7468
0.6-0.7	4262
0.7-0.8	517
0.8-0.85	22
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC245004
0.9759	High Similarity	NPC131329
0.9157	High Similarity	NPC471408
0.9059	High Similarity	NPC35933
0.8864	High Similarity	NPC246028
0.8824	High Similarity	NPC49208
0.8824	High Similarity	NPC23748
0.8696	High Similarity	NPC57664
0.8667	High Similarity	NPC477574
0.8588	High Similarity	NPC25554
0.8571	High Similarity	NPC53555
0.8478	Intermediate Similarity	NPC472416
0.8478	Intermediate Similarity	NPC472360
0.8444	Intermediate Similarity	NPC82876
0.8427	Intermediate Similarity	NPC166857
0.8421	Intermediate Similarity	NPC38855
0.8421	Intermediate Similarity	NPC473510
0.8404	Intermediate Similarity	NPC473244
0.8404	Intermediate Similarity	NPC210337
0.837	Intermediate Similarity	NPC27918
0.8353	Intermediate Similarity	NPC242767
0.8352	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC40049
0.8316	Intermediate Similarity	NPC247233
0.8315	Intermediate Similarity	NPC175145
0.8315	Intermediate Similarity	NPC475069
0.8298	Intermediate Similarity	NPC221801
0.8298	Intermediate Similarity	NPC129569
0.8298	Intermediate Similarity	NPC211810
0.8298	Intermediate Similarity	NPC284194
0.8298	Intermediate Similarity	NPC471765
0.8298	Intermediate Similarity	NPC88009
0.8276	Intermediate Similarity	NPC256112
0.8261	Intermediate Similarity	NPC177641
0.8256	Intermediate Similarity	NPC233332
0.8247	Intermediate Similarity	NPC11956
0.8242	Intermediate Similarity	NPC16265
0.8229	Intermediate Similarity	NPC230546
0.8182	Intermediate Similarity	NPC476927
0.8163	Intermediate Similarity	NPC23584
0.8161	Intermediate Similarity	NPC142163
0.8152	Intermediate Similarity	NPC220216
0.8144	Intermediate Similarity	NPC472554
0.8144	Intermediate Similarity	NPC475617
0.814	Intermediate Similarity	NPC233295
0.8118	Intermediate Similarity	NPC283619
0.8111	Intermediate Similarity	NPC281316
0.8105	Intermediate Similarity	NPC473153
0.81	Intermediate Similarity	NPC301666
0.8085	Intermediate Similarity	NPC474922
0.8085	Intermediate Similarity	NPC182826
0.8085	Intermediate Similarity	NPC469491
0.8085	Intermediate Similarity	NPC105375
0.8081	Intermediate Similarity	NPC473543
0.8068	Intermediate Similarity	NPC2524
0.8065	Intermediate Similarity	NPC124374
0.8065	Intermediate Similarity	NPC41239
0.8061	Intermediate Similarity	NPC472552
0.8046	Intermediate Similarity	NPC474592
0.8043	Intermediate Similarity	NPC115607
0.8043	Intermediate Similarity	NPC49783
0.8043	Intermediate Similarity	NPC261320
0.8041	Intermediate Similarity	NPC79303
0.8041	Intermediate Similarity	NPC188968
0.8041	Intermediate Similarity	NPC474190
0.8022	Intermediate Similarity	NPC476948
0.8022	Intermediate Similarity	NPC471779
0.8021	Intermediate Similarity	NPC205143
0.8021	Intermediate Similarity	NPC254496
0.8	Intermediate Similarity	NPC109528
0.8	Intermediate Similarity	NPC53565
0.8	Intermediate Similarity	NPC276110
0.8	Intermediate Similarity	NPC265588
0.798	Intermediate Similarity	NPC473523
0.798	Intermediate Similarity	NPC474124
0.7979	Intermediate Similarity	NPC99653
0.7978	Intermediate Similarity	NPC52108
0.7978	Intermediate Similarity	NPC474789
0.7978	Intermediate Similarity	NPC474809
0.7959	Intermediate Similarity	NPC280991
0.7959	Intermediate Similarity	NPC303559
0.7957	Intermediate Similarity	NPC472307
0.7957	Intermediate Similarity	NPC473269
0.7955	Intermediate Similarity	NPC159148
0.7955	Intermediate Similarity	NPC170303
0.7941	Intermediate Similarity	NPC472216
0.7941	Intermediate Similarity	NPC5475
0.7941	Intermediate Similarity	NPC284828
0.7941	Intermediate Similarity	NPC173905
0.7938	Intermediate Similarity	NPC278386
0.7938	Intermediate Similarity	NPC124512
0.7938	Intermediate Similarity	NPC159763
0.7931	Intermediate Similarity	NPC100906
0.7921	Intermediate Similarity	NPC475176
0.7921	Intermediate Similarity	NPC67321
0.7921	Intermediate Similarity	NPC187435
0.7917	Intermediate Similarity	NPC288970
0.7917	Intermediate Similarity	NPC190713
0.7912	Intermediate Similarity	NPC255143
0.7912	Intermediate Similarity	NPC473226
0.7912	Intermediate Similarity	NPC474970
0.7912	Intermediate Similarity	NPC131813
0.7912	Intermediate Similarity	NPC329692
0.7895	Intermediate Similarity	NPC215700
0.7895	Intermediate Similarity	NPC105490
0.7889	Intermediate Similarity	NPC302360
0.7889	Intermediate Similarity	NPC306951
0.7889	Intermediate Similarity	NPC102048
0.7889	Intermediate Similarity	NPC83702
0.7879	Intermediate Similarity	NPC273668
0.7879	Intermediate Similarity	NPC472815
0.7879	Intermediate Similarity	NPC283343
0.7879	Intermediate Similarity	NPC258547
0.7879	Intermediate Similarity	NPC470571
0.7879	Intermediate Similarity	NPC476471
0.7879	Intermediate Similarity	NPC475344
0.7872	Intermediate Similarity	NPC234335
0.7872	Intermediate Similarity	NPC329842
0.7872	Intermediate Similarity	NPC475972
0.7872	Intermediate Similarity	NPC472811
0.7872	Intermediate Similarity	NPC303697
0.7865	Intermediate Similarity	NPC155521
0.7865	Intermediate Similarity	NPC471218
0.7857	Intermediate Similarity	NPC271295
0.7849	Intermediate Similarity	NPC97103
0.7849	Intermediate Similarity	NPC473647
0.7849	Intermediate Similarity	NPC314727
0.7843	Intermediate Similarity	NPC128795
0.7843	Intermediate Similarity	NPC217921
0.7843	Intermediate Similarity	NPC306265
0.7843	Intermediate Similarity	NPC135015
0.7843	Intermediate Similarity	NPC48548
0.7843	Intermediate Similarity	NPC50124
0.7843	Intermediate Similarity	NPC38948
0.7841	Intermediate Similarity	NPC281880
0.7835	Intermediate Similarity	NPC91197
0.7835	Intermediate Similarity	NPC254121
0.7835	Intermediate Similarity	NPC239547
0.7835	Intermediate Similarity	NPC96597
0.7835	Intermediate Similarity	NPC309503
0.7835	Intermediate Similarity	NPC73911
0.7835	Intermediate Similarity	NPC141401
0.7835	Intermediate Similarity	NPC155319
0.7835	Intermediate Similarity	NPC125551
0.7835	Intermediate Similarity	NPC285513
0.7826	Intermediate Similarity	NPC473891
0.7826	Intermediate Similarity	NPC149224
0.7822	Intermediate Similarity	NPC88349
0.7822	Intermediate Similarity	NPC173172
0.7822	Intermediate Similarity	NPC470763
0.7822	Intermediate Similarity	NPC475414
0.7822	Intermediate Similarity	NPC470767
0.7816	Intermediate Similarity	NPC167891
0.7816	Intermediate Similarity	NPC137587
0.7816	Intermediate Similarity	NPC83351
0.7812	Intermediate Similarity	NPC472441
0.7812	Intermediate Similarity	NPC134067
0.7812	Intermediate Similarity	NPC8774
0.7812	Intermediate Similarity	NPC476720
0.7802	Intermediate Similarity	NPC477578
0.7802	Intermediate Similarity	NPC274448
0.7802	Intermediate Similarity	NPC164424
0.7802	Intermediate Similarity	NPC11804
0.78	Intermediate Similarity	NPC99266
0.7789	Intermediate Similarity	NPC472812
0.7789	Intermediate Similarity	NPC162615
0.7789	Intermediate Similarity	NPC205034
0.7789	Intermediate Similarity	NPC152778
0.7789	Intermediate Similarity	NPC7349
0.7788	Intermediate Similarity	NPC324683
0.7778	Intermediate Similarity	NPC57370
0.7778	Intermediate Similarity	NPC96784
0.7778	Intermediate Similarity	NPC235920
0.7778	Intermediate Similarity	NPC473160
0.7778	Intermediate Similarity	NPC79945
0.7778	Intermediate Similarity	NPC11974
0.7767	Intermediate Similarity	NPC206618
0.7767	Intermediate Similarity	NPC475065
0.7767	Intermediate Similarity	NPC475586
0.7767	Intermediate Similarity	NPC40728
0.7767	Intermediate Similarity	NPC316974
0.7766	Intermediate Similarity	NPC48732
0.7766	Intermediate Similarity	NPC182136
0.7766	Intermediate Similarity	NPC310479
0.7766	Intermediate Similarity	NPC221111
0.7766	Intermediate Similarity	NPC295668
0.7766	Intermediate Similarity	NPC280149
0.7765	Intermediate Similarity	NPC104644
0.7755	Intermediate Similarity	NPC92275
0.7755	Intermediate Similarity	NPC316598
0.7755	Intermediate Similarity	NPC478056
0.7755	Intermediate Similarity	NPC218107
0.7753	Intermediate Similarity	NPC475944
0.7745	Intermediate Similarity	NPC330011
0.7745	Intermediate Similarity	NPC88013
0.7745	Intermediate Similarity	NPC472390
0.7745	Intermediate Similarity	NPC473586
0.7745	Intermediate Similarity	NPC125423
0.7745	Intermediate Similarity	NPC329048
0.7742	Intermediate Similarity	NPC7280

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 NPC20946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1700
0.2-0.3	3706
0.3-0.4	2398
0.4-0.5	788
0.5-0.6	325
0.6-0.7	69
0.7-0.8	8
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
0.7938	Intermediate Similarity	NPD4225	Approved
0.76	Intermediate Similarity	NPD5344	Discontinued
0.7593	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7471	Intermediate Similarity	NPD8264	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.7245	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.7128	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6051	Approved
0.7103	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD7748	Approved
0.697	Remote Similarity	NPD7515	Phase 2
0.6957	Remote Similarity	NPD7645	Phase 2
0.6939	Remote Similarity	NPD6101	Approved
0.6939	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7524	Approved
0.6903	Remote Similarity	NPD7327	Approved
0.6903	Remote Similarity	NPD7328	Approved
0.69	Remote Similarity	NPD6399	Phase 3
0.6882	Remote Similarity	NPD7525	Registered
0.6875	Remote Similarity	NPD1694	Approved
0.687	Remote Similarity	NPD7503	Approved
0.687	Remote Similarity	NPD8033	Approved
0.6869	Remote Similarity	NPD7838	Discovery
0.6852	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7516	Approved
0.68	Remote Similarity	NPD7637	Suspended
0.6796	Remote Similarity	NPD7902	Approved
0.6783	Remote Similarity	NPD8294	Approved
0.6783	Remote Similarity	NPD8377	Approved
0.6762	Remote Similarity	NPD4159	Approved
0.6757	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD8379	Approved
0.6724	Remote Similarity	NPD8378	Approved
0.6724	Remote Similarity	NPD8296	Approved
0.6724	Remote Similarity	NPD8380	Approved
0.6724	Remote Similarity	NPD8335	Approved
0.6703	Remote Similarity	NPD7339	Approved
0.6703	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD6698	Approved
0.67	Remote Similarity	NPD46	Approved
0.6699	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD6686	Approved
0.6697	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6933	Approved
0.663	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5697	Approved
0.6598	Remote Similarity	NPD4786	Approved
0.6598	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8516	Approved
0.6581	Remote Similarity	NPD8515	Approved
0.6581	Remote Similarity	NPD8513	Phase 3
0.6581	Remote Similarity	NPD8517	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6566	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3667	Approved
0.6549	Remote Similarity	NPD4632	Approved
0.6545	Remote Similarity	NPD6011	Approved
0.6545	Remote Similarity	NPD7320	Approved
0.6535	Remote Similarity	NPD5785	Approved
0.6526	Remote Similarity	NPD4822	Approved
0.6526	Remote Similarity	NPD4748	Discontinued
0.6526	Remote Similarity	NPD4819	Approved
0.6526	Remote Similarity	NPD4821	Approved
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4820	Approved
0.6522	Remote Similarity	NPD8039	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6512	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7900	Approved
0.65	Remote Similarity	NPD7507	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6495	Remote Similarity	NPD5362	Discontinued
0.6489	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6013	Approved
0.6486	Remote Similarity	NPD6373	Approved
0.6486	Remote Similarity	NPD6012	Approved
0.6486	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6083	Phase 2
0.6476	Remote Similarity	NPD6084	Phase 2
0.6471	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD368	Approved
0.6471	Remote Similarity	NPD6079	Approved
0.6465	Remote Similarity	NPD3618	Phase 1
0.646	Remote Similarity	NPD6882	Approved
0.6455	Remote Similarity	NPD5701	Approved
0.6455	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5695	Phase 3
0.6436	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD6371	Approved
0.6413	Remote Similarity	NPD6926	Approved
0.6413	Remote Similarity	NPD6924	Approved
0.64	Remote Similarity	NPD7750	Discontinued
0.64	Remote Similarity	NPD3573	Approved
0.6389	Remote Similarity	NPD5211	Phase 2
0.6372	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1696	Phase 3
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6319	Approved
0.6354	Remote Similarity	NPD6931	Approved
0.6354	Remote Similarity	NPD6930	Phase 2
0.6354	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7332	Phase 2
0.6354	Remote Similarity	NPD7514	Phase 3
0.6341	Remote Similarity	NPD7319	Approved
0.6327	Remote Similarity	NPD5332	Approved
0.6327	Remote Similarity	NPD5331	Approved
0.6316	Remote Similarity	NPD4271	Approved
0.6316	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD8034	Phase 2
0.6311	Remote Similarity	NPD8074	Phase 3
0.6311	Remote Similarity	NPD8035	Phase 2
0.63	Remote Similarity	NPD7146	Approved
0.63	Remote Similarity	NPD7334	Approved
0.63	Remote Similarity	NPD6409	Approved
0.63	Remote Similarity	NPD7521	Approved
0.63	Remote Similarity	NPD5330	Approved
0.63	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD4790	Discontinued
0.6275	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5141	Approved
0.6261	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6929	Approved
0.625	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4784	Approved
0.6237	Remote Similarity	NPD4785	Approved
0.6226	Remote Similarity	NPD5222	Approved
0.6226	Remote Similarity	NPD5221	Approved
0.6226	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4269	Approved
0.6224	Remote Similarity	NPD4270	Approved
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD7604	Phase 2
0.6196	Remote Similarity	NPD7151	Approved
0.6196	Remote Similarity	NPD7150	Approved
0.6196	Remote Similarity	NPD7152	Approved
0.6186	Remote Similarity	NPD6335	Approved
0.6186	Remote Similarity	NPD7509	Discontinued
0.6176	Remote Similarity	NPD6672	Approved
0.6176	Remote Similarity	NPD5737	Approved
0.6176	Remote Similarity	NPD6903	Approved
0.6176	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5173	Approved
0.6168	Remote Similarity	NPD4755	Approved
0.6167	Remote Similarity	NPD6921	Approved
0.6167	Remote Similarity	NPD5983	Phase 2
0.6161	Remote Similarity	NPD6412	Phase 2
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD7087	Discontinued
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD6868	Approved
0.6148	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD5223	Approved
0.6146	Remote Similarity	NPD7145	Approved
0.6139	Remote Similarity	NPD5786	Approved
0.6139	Remote Similarity	NPD4623	Approved
0.6139	Remote Similarity	NPD4519	Discontinued
0.6134	Remote Similarity	NPD7100	Approved
0.6134	Remote Similarity	NPD7101	Approved
0.6132	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5369	Approved
0.6122	Remote Similarity	NPD6902	Approved
0.6111	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD5696	Approved
0.6102	Remote Similarity	NPD6317	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