NPASS Compound

Structure

CID130665 OpenBabel06191715492D 22 23 0 0 1 0 0 0 0 0999 V2000 -3.4744 -5.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6559 -2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -4.8978 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 -0.0000 -2.0000 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 -1.2838 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0249 -2.7071 0.0000 C 0 0 0 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 -2.5981 -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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 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 -2.2497 -3.9319 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2156 -3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 14 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 6 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 1 0 0 0 19 22 1 0 0 0 0 20 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	347.034
LogP:	3.976
LogD:	3.344
LogS:	-4.551
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	4.93
Fsp3:	0.7
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:	-4.647
MDCK Permeability:	1.1873591574840248e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	93.3027114868164%
Volume Distribution (VD):	1.791
Pgp-substrate:	10.11841869354248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.462
CYP2C19-inhibitor:	0.255
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.623
CYP2D6-inhibitor:	0.278
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	3.964
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.684
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.502
Skin Sensitization:	0.951
Carcinogencity:	0.214
Eye Corrosion:	0.05
Eye Irritation:	0.227
Respiratory Toxicity:	0.792

Download Data

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

Natural Product: NPC130665

Natural Product ID:	NPC130665
*Common Name:**	Vitetrifolin G
IUPAC Name:	(2S,3S,4R)-4-(3-hydroxy-3-methylpent-4-enyl)-3,4,8,8-tetramethyl-2,3,6,7-tetrahydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	CYPPFALFRDZTNG-NBHCPLFVSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-7-19(5,22)11-12-20(6)14(2)17(21)13-16-15(20)9-8-10-18(16,3)4/h7,9,13-14,17,21-22H,1,8,10-12H2,2-6H3/t14-,17+,19?,20-/m1/s1
SMILES:	C=CC(CC[C@]1(C)[C@H](C)[C@@H](O)C=C2C1=CCCC2(C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436604
PubChem CID:	10892069
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[515542]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	34100.0	nM	PMID[515542]

☑ 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 NPC130665 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	172
0.1-0.2	1277
0.2-0.3	6895
0.3-0.4	16704
0.4-0.5	9987
0.5-0.6	5613
0.6-0.7	1698
0.7-0.8	330
0.8-0.85	15
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC471560
0.8857	High Similarity	NPC34834
0.863	High Similarity	NPC171148
0.863	High Similarity	NPC313179
0.863	High Similarity	NPC69383
0.859	High Similarity	NPC231310
0.859	High Similarity	NPC238485
0.8514	High Similarity	NPC265588
0.8462	Intermediate Similarity	NPC470384
0.8429	Intermediate Similarity	NPC114651
0.84	Intermediate Similarity	NPC91594
0.8333	Intermediate Similarity	NPC202389
0.8333	Intermediate Similarity	NPC87489
0.8333	Intermediate Similarity	NPC471408
0.831	Intermediate Similarity	NPC216460
0.831	Intermediate Similarity	NPC32055
0.8289	Intermediate Similarity	NPC167891
0.8289	Intermediate Similarity	NPC83351
0.8286	Intermediate Similarity	NPC279434
0.8267	Intermediate Similarity	NPC106432
0.8243	Intermediate Similarity	NPC201048
0.8243	Intermediate Similarity	NPC476366
0.8219	Intermediate Similarity	NPC110799
0.8205	Intermediate Similarity	NPC264245
0.8194	Intermediate Similarity	NPC473893
0.8194	Intermediate Similarity	NPC474248
0.8169	Intermediate Similarity	NPC68703
0.8169	Intermediate Similarity	NPC69649
0.8158	Intermediate Similarity	NPC470758
0.8158	Intermediate Similarity	NPC470711
0.8143	Intermediate Similarity	NPC163678
0.8143	Intermediate Similarity	NPC308844
0.8133	Intermediate Similarity	NPC32832
0.8108	Intermediate Similarity	NPC471799
0.8108	Intermediate Similarity	NPC68443
0.8101	Intermediate Similarity	NPC49964
0.8088	Intermediate Similarity	NPC66020
0.8077	Intermediate Similarity	NPC241290
0.8077	Intermediate Similarity	NPC209944
0.8077	Intermediate Similarity	NPC234193
0.8077	Intermediate Similarity	NPC164840
0.8056	Intermediate Similarity	NPC208999
0.8056	Intermediate Similarity	NPC96484
0.8052	Intermediate Similarity	NPC72507
0.8028	Intermediate Similarity	NPC476406
0.8028	Intermediate Similarity	NPC267027
0.8028	Intermediate Similarity	NPC202017
0.8028	Intermediate Similarity	NPC149680
0.8026	Intermediate Similarity	NPC244488
0.8026	Intermediate Similarity	NPC253190
0.8026	Intermediate Similarity	NPC247325
0.8026	Intermediate Similarity	NPC470749
0.8025	Intermediate Similarity	NPC109528
0.8	Intermediate Similarity	NPC471797
0.8	Intermediate Similarity	NPC306727
0.7975	Intermediate Similarity	NPC249423
0.7975	Intermediate Similarity	NPC476646
0.7975	Intermediate Similarity	NPC47761
0.7975	Intermediate Similarity	NPC6663
0.7975	Intermediate Similarity	NPC6707
0.7973	Intermediate Similarity	NPC242001
0.7973	Intermediate Similarity	NPC23954
0.7973	Intermediate Similarity	NPC167706
0.7952	Intermediate Similarity	NPC280556
0.7949	Intermediate Similarity	NPC30986
0.7949	Intermediate Similarity	NPC84694
0.7949	Intermediate Similarity	NPC143182
0.7949	Intermediate Similarity	NPC28862
0.7949	Intermediate Similarity	NPC47982
0.7949	Intermediate Similarity	NPC81306
0.7949	Intermediate Similarity	NPC209430
0.7949	Intermediate Similarity	NPC109546
0.7945	Intermediate Similarity	NPC9942
0.7917	Intermediate Similarity	NPC197805
0.7917	Intermediate Similarity	NPC171225
0.7901	Intermediate Similarity	NPC205845
0.7895	Intermediate Similarity	NPC471468
0.7875	Intermediate Similarity	NPC296701
0.7875	Intermediate Similarity	NPC50964
0.7875	Intermediate Similarity	NPC218616
0.7867	Intermediate Similarity	NPC265485
0.7867	Intermediate Similarity	NPC182717
0.7867	Intermediate Similarity	NPC474140
0.7867	Intermediate Similarity	NPC220939
0.7857	Intermediate Similarity	NPC174956
0.7848	Intermediate Similarity	NPC295131
0.7848	Intermediate Similarity	NPC96362
0.7838	Intermediate Similarity	NPC145498
0.7831	Intermediate Similarity	NPC245004
0.7821	Intermediate Similarity	NPC18603
0.7821	Intermediate Similarity	NPC11908
0.7821	Intermediate Similarity	NPC474216
0.7821	Intermediate Similarity	NPC307965
0.7821	Intermediate Similarity	NPC76931
0.7821	Intermediate Similarity	NPC318136
0.7821	Intermediate Similarity	NPC186191
0.7821	Intermediate Similarity	NPC476314
0.7821	Intermediate Similarity	NPC205455
0.7808	Intermediate Similarity	NPC471238
0.7805	Intermediate Similarity	NPC274448
0.7792	Intermediate Similarity	NPC470362
0.7791	Intermediate Similarity	NPC310013
0.7778	Intermediate Similarity	NPC474634
0.7778	Intermediate Similarity	NPC475789
0.7778	Intermediate Similarity	NPC476039
0.7778	Intermediate Similarity	NPC286669
0.7778	Intermediate Similarity	NPC222366
0.7778	Intermediate Similarity	NPC237795
0.7778	Intermediate Similarity	NPC82538
0.7763	Intermediate Similarity	NPC329090
0.7763	Intermediate Similarity	NPC91858
0.7763	Intermediate Similarity	NPC477138
0.7763	Intermediate Similarity	NPC27395
0.7763	Intermediate Similarity	NPC243342
0.775	Intermediate Similarity	NPC209620
0.775	Intermediate Similarity	NPC23852
0.7746	Intermediate Similarity	NPC107540
0.7746	Intermediate Similarity	NPC323424
0.7746	Intermediate Similarity	NPC300593
0.7746	Intermediate Similarity	NPC309300
0.7746	Intermediate Similarity	NPC290367
0.7746	Intermediate Similarity	NPC96793
0.7733	Intermediate Similarity	NPC164022
0.7733	Intermediate Similarity	NPC95863
0.7733	Intermediate Similarity	NPC471272
0.7722	Intermediate Similarity	NPC233295
0.7722	Intermediate Similarity	NPC242767
0.7714	Intermediate Similarity	NPC68679
0.7714	Intermediate Similarity	NPC475251
0.7714	Intermediate Similarity	NPC321867
0.7714	Intermediate Similarity	NPC207007
0.7714	Intermediate Similarity	NPC469728
0.7714	Intermediate Similarity	NPC225342
0.7711	Intermediate Similarity	NPC281316
0.7711	Intermediate Similarity	NPC261266
0.7703	Intermediate Similarity	NPC329989
0.7703	Intermediate Similarity	NPC476431
0.7703	Intermediate Similarity	NPC239373
0.7692	Intermediate Similarity	NPC477427
0.7692	Intermediate Similarity	NPC474826
0.7692	Intermediate Similarity	NPC471798
0.7692	Intermediate Similarity	NPC477426
0.7692	Intermediate Similarity	NPC198968
0.7692	Intermediate Similarity	NPC214570
0.7692	Intermediate Similarity	NPC318495
0.7692	Intermediate Similarity	NPC477425
0.7692	Intermediate Similarity	NPC155986
0.7683	Intermediate Similarity	NPC470077
0.7683	Intermediate Similarity	NPC474047
0.7681	Intermediate Similarity	NPC475931
0.7681	Intermediate Similarity	NPC122239
0.7671	Intermediate Similarity	NPC45782
0.7662	Intermediate Similarity	NPC133580
0.7662	Intermediate Similarity	NPC328104
0.7662	Intermediate Similarity	NPC291503
0.7662	Intermediate Similarity	NPC319090
0.7654	Intermediate Similarity	NPC201852
0.7654	Intermediate Similarity	NPC224455
0.7654	Intermediate Similarity	NPC20853
0.7654	Intermediate Similarity	NPC101462
0.7654	Intermediate Similarity	NPC155521
0.7654	Intermediate Similarity	NPC189972
0.7647	Intermediate Similarity	NPC20946
0.7647	Intermediate Similarity	NPC16265
0.7639	Intermediate Similarity	NPC19569
0.7632	Intermediate Similarity	NPC474743
0.7632	Intermediate Similarity	NPC329763
0.7625	Intermediate Similarity	NPC324772
0.7625	Intermediate Similarity	NPC474592
0.7619	Intermediate Similarity	NPC149224
0.7619	Intermediate Similarity	NPC287079
0.7619	Intermediate Similarity	NPC131329
0.7606	Intermediate Similarity	NPC81615
0.76	Intermediate Similarity	NPC92801
0.7595	Intermediate Similarity	NPC473943
0.7595	Intermediate Similarity	NPC275910
0.7595	Intermediate Similarity	NPC477514
0.759	Intermediate Similarity	NPC470360
0.759	Intermediate Similarity	NPC157257
0.759	Intermediate Similarity	NPC474083
0.759	Intermediate Similarity	NPC318390
0.7571	Intermediate Similarity	NPC240506
0.7571	Intermediate Similarity	NPC176621
0.7564	Intermediate Similarity	NPC73875
0.7564	Intermediate Similarity	NPC113733
0.7564	Intermediate Similarity	NPC129165
0.7564	Intermediate Similarity	NPC315261
0.7564	Intermediate Similarity	NPC46160
0.7564	Intermediate Similarity	NPC321016
0.7564	Intermediate Similarity	NPC321381
0.7564	Intermediate Similarity	NPC107059
0.7564	Intermediate Similarity	NPC134330
0.7564	Intermediate Similarity	NPC310643
0.7564	Intermediate Similarity	NPC202642
0.7564	Intermediate Similarity	NPC471658
0.7561	Intermediate Similarity	NPC82623
0.7561	Intermediate Similarity	NPC52108
0.7561	Intermediate Similarity	NPC57370
0.7561	Intermediate Similarity	NPC474789
0.7561	Intermediate Similarity	NPC317458

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 NPC130665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1837
0.2-0.3	3971
0.3-0.4	2248
0.4-0.5	655
0.5-0.6	201
0.6-0.7	62
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.863	High Similarity	NPD8264	Approved
0.7821	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6924	Approved
0.7763	Intermediate Similarity	NPD6926	Approved
0.7714	Intermediate Similarity	NPD368	Approved
0.7625	Intermediate Similarity	NPD6931	Approved
0.7625	Intermediate Similarity	NPD7332	Phase 2
0.7625	Intermediate Similarity	NPD6930	Phase 2
0.7625	Intermediate Similarity	NPD7514	Phase 3
0.7564	Intermediate Similarity	NPD6933	Approved
0.75	Intermediate Similarity	NPD6929	Approved
0.7436	Intermediate Similarity	NPD6942	Approved
0.7436	Intermediate Similarity	NPD7339	Approved
0.7375	Intermediate Similarity	NPD7145	Approved
0.7368	Intermediate Similarity	NPD7144	Approved
0.7368	Intermediate Similarity	NPD7143	Approved
0.7353	Intermediate Similarity	NPD342	Phase 1
0.7349	Intermediate Similarity	NPD6695	Phase 3
0.7342	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6902	Approved
0.7284	Intermediate Similarity	NPD7645	Phase 2
0.7273	Intermediate Similarity	NPD7150	Approved
0.7273	Intermediate Similarity	NPD7152	Approved
0.7273	Intermediate Similarity	NPD7151	Approved
0.7262	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6932	Approved
0.725	Intermediate Similarity	NPD5776	Phase 2
0.725	Intermediate Similarity	NPD6925	Approved
0.7246	Intermediate Similarity	NPD4219	Approved
0.7237	Intermediate Similarity	NPD6923	Approved
0.7237	Intermediate Similarity	NPD6922	Approved
0.7209	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7525	Registered
0.7195	Intermediate Similarity	NPD7509	Discontinued
0.7176	Intermediate Similarity	NPD6893	Approved
0.7108	Intermediate Similarity	NPD6898	Phase 1
0.7089	Intermediate Similarity	NPD4785	Approved
0.7089	Intermediate Similarity	NPD4784	Approved
0.7051	Intermediate Similarity	NPD4243	Approved
0.7011	Intermediate Similarity	NPD7750	Discontinued
0.7011	Intermediate Similarity	NPD7524	Approved
0.6988	Remote Similarity	NPD4748	Discontinued
0.6962	Remote Similarity	NPD4732	Discontinued
0.6897	Remote Similarity	NPD5279	Phase 3
0.6867	Remote Similarity	NPD6683	Phase 2
0.686	Remote Similarity	NPD4786	Approved
0.6824	Remote Similarity	NPD3667	Approved
0.6813	Remote Similarity	NPD5778	Approved
0.6813	Remote Similarity	NPD5779	Approved
0.6782	Remote Similarity	NPD1696	Phase 3
0.6705	Remote Similarity	NPD4623	Approved
0.6705	Remote Similarity	NPD4519	Discontinued
0.6703	Remote Similarity	NPD6411	Approved
0.6703	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6588	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4190	Phase 3
0.6585	Remote Similarity	NPD5275	Approved
0.6548	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6079	Approved
0.6522	Remote Similarity	NPD7637	Suspended
0.6517	Remote Similarity	NPD3618	Phase 1
0.6517	Remote Similarity	NPD4694	Approved
0.6517	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD6101	Approved
0.6484	Remote Similarity	NPD5328	Approved
0.6484	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7136	Phase 2
0.6395	Remote Similarity	NPD4820	Approved
0.6395	Remote Similarity	NPD4819	Approved
0.6395	Remote Similarity	NPD4822	Approved
0.6395	Remote Similarity	NPD4821	Approved
0.6344	Remote Similarity	NPD5284	Approved
0.6344	Remote Similarity	NPD7515	Phase 2
0.6344	Remote Similarity	NPD5281	Approved
0.6333	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD4194	Approved
0.6316	Remote Similarity	NPD4193	Approved
0.6316	Remote Similarity	NPD4191	Approved
0.6316	Remote Similarity	NPD4192	Approved
0.6304	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4753	Phase 2
0.6304	Remote Similarity	NPD6051	Approved
0.6277	Remote Similarity	NPD4202	Approved
0.6263	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4223	Phase 3
0.625	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD7640	Approved
0.6222	Remote Similarity	NPD5329	Approved
0.6196	Remote Similarity	NPD4518	Approved
0.619	Remote Similarity	NPD8039	Approved
0.6184	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5331	Approved
0.618	Remote Similarity	NPD5332	Approved
0.618	Remote Similarity	NPD5362	Discontinued
0.6163	Remote Similarity	NPD4271	Approved
0.6163	Remote Similarity	NPD4268	Approved
0.6154	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4629	Approved
0.6146	Remote Similarity	NPD5210	Approved
0.6139	Remote Similarity	NPD5141	Approved
0.6136	Remote Similarity	NPD4692	Approved
0.6136	Remote Similarity	NPD4790	Discontinued
0.6136	Remote Similarity	NPD4139	Approved
0.6122	Remote Similarity	NPD7638	Approved
0.6111	Remote Similarity	NPD3668	Phase 3
0.6111	Remote Similarity	NPD4197	Approved
0.6111	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6399	Phase 3
0.6105	Remote Similarity	NPD5133	Approved
0.6082	Remote Similarity	NPD5222	Approved
0.6082	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5221	Approved
0.6076	Remote Similarity	NPD7341	Phase 2
0.6067	Remote Similarity	NPD4270	Approved
0.6067	Remote Similarity	NPD4269	Approved
0.6064	Remote Similarity	NPD4096	Approved
0.6064	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5286	Approved
0.6061	Remote Similarity	NPD5285	Approved
0.6061	Remote Similarity	NPD4696	Approved
0.6061	Remote Similarity	NPD6404	Discontinued
0.6044	Remote Similarity	NPD1694	Approved
0.6042	Remote Similarity	NPD7748	Approved
0.6029	Remote Similarity	NPD4265	Approved
0.6023	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4695	Discontinued
0.602	Remote Similarity	NPD6084	Phase 2
0.602	Remote Similarity	NPD4755	Approved
0.602	Remote Similarity	NPD5173	Approved
0.602	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD8262	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7154	Phase 3
0.5979	Remote Similarity	NPD5695	Phase 3
0.5978	Remote Similarity	NPD5330	Approved
0.5978	Remote Similarity	NPD7334	Approved
0.5978	Remote Similarity	NPD6684	Approved
0.5978	Remote Similarity	NPD7146	Approved
0.5978	Remote Similarity	NPD4693	Phase 3
0.5978	Remote Similarity	NPD4689	Approved
0.5978	Remote Similarity	NPD5205	Approved
0.5978	Remote Similarity	NPD7521	Approved
0.5978	Remote Similarity	NPD4690	Approved
0.5978	Remote Similarity	NPD4138	Approved
0.5978	Remote Similarity	NPD4688	Approved
0.5978	Remote Similarity	NPD6409	Approved
0.5978	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD3617	Approved
0.596	Remote Similarity	NPD5290	Discontinued
0.596	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4225	Approved
0.5941	Remote Similarity	NPD4633	Approved
0.5941	Remote Similarity	NPD5224	Approved
0.5941	Remote Similarity	NPD5226	Approved
0.5941	Remote Similarity	NPD5225	Approved
0.5918	Remote Similarity	NPD4697	Phase 3
0.59	Remote Similarity	NPD4700	Approved
0.5895	Remote Similarity	NPD5785	Approved
0.5895	Remote Similarity	NPD5207	Approved
0.5895	Remote Similarity	NPD7838	Discovery
0.5882	Remote Similarity	NPD5175	Approved
0.5882	Remote Similarity	NPD5174	Approved
0.5882	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5733	Approved
0.5882	Remote Similarity	NPD4687	Approved
0.587	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5363	Approved
0.5859	Remote Similarity	NPD7902	Approved
0.5851	Remote Similarity	NPD4722	Approved
0.5851	Remote Similarity	NPD6903	Approved
0.5851	Remote Similarity	NPD4723	Approved
0.5851	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4252	Approved
0.5842	Remote Similarity	NPD4159	Approved
0.5833	Remote Similarity	NPD7983	Approved
0.5833	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD6050	Approved
0.5818	Remote Similarity	NPD7115	Discovery
0.581	Remote Similarity	NPD6881	Approved
0.581	Remote Similarity	NPD6899	Approved
0.5806	Remote Similarity	NPD5786	Approved
0.5784	Remote Similarity	NPD7632	Discontinued
0.5783	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5369	Approved
0.5769	Remote Similarity	NPD6640	Phase 3
0.5769	Remote Similarity	NPD7128	Approved
0.5769	Remote Similarity	NPD6402	Approved
0.5769	Remote Similarity	NPD5739	Approved
0.5769	Remote Similarity	NPD6675	Approved
0.5758	Remote Similarity	NPD7839	Suspended
0.5752	Remote Similarity	NPD7503	Approved
0.5747	Remote Similarity	NPD1346	Approved
0.5743	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