NPASS Compound

Structure

NPC471408 OpenBabel07101719142D 24 25 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 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 -0.8660 1.5000 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 -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 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 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 7 24 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 15 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 6 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 1 0 0 0 18 24 1 1 0 0 0 20 23 1 0 0 0 0 21 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.27
Volume:	375.757
LogP:	3.772
LogD:	3.022
LogS:	-4.533
# Rotatable Bonds:	5
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	4.92
Fsp3:	0.81
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:	-4.549
MDCK Permeability:	1.4341851965582464e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.217
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.453
Plasma Protein Binding (PPB):	91.36769104003906%
Volume Distribution (VD):	1.679
Pgp-substrate:	10.90211009979248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.16
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.458

ADMET: Excretion

Clearance (CL):	6.435
Half-life (T1/2):	0.052

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.106
Carcinogencity:	0.067
Eye Corrosion:	0.031
Eye Irritation:	0.263
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC471408

Natural Product ID:	NPC471408
*Common Name:**	(Rel 6S,7R,8S,9R)-6-Methoxy-5(10),14-Halimadien-7,13-Diol
IUPAC Name:	(1S,2R,3S,4R)-4-(3-hydroxy-3-methylpent-4-enyl)-1-methoxy-3,4,8,8-tetramethyl-1,2,3,5,6,7-hexahydronaphthalen-2-ol
Synonyms:
Standard InCHIKey:	MOSBXEUBWDRPSK-LJLVOHHFSA-N
Standard InCHI:	InChI=1S/C21H36O3/c1-8-20(5,23)12-13-21(6)14(2)17(22)18(24-7)16-15(21)10-9-11-19(16,3)4/h8,14,17-18,22-23H,1,9-13H2,2-7H3/t14-,17-,18+,20?,21-/m1/s1
SMILES:	CC1C(C(C2=C(C1(C)CCC(C)(C=C)O)CCCC2(C)C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436603
PubChem CID:	72375122
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]
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[546024]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	22200.0	nM	PMID[546024]

☑ 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 NPC471408 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	187
0.1-0.2	1489
0.2-0.3	5467
0.3-0.4	15550
0.4-0.5	10762
0.5-0.6	6860
0.6-0.7	2118
0.7-0.8	244
0.8-0.85	11
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC20946
0.8916	High Similarity	NPC131329
0.8916	High Similarity	NPC245004
0.8718	High Similarity	NPC265588
0.8625	High Similarity	NPC233295
0.8571	High Similarity	NPC281316
0.8519	High Similarity	NPC474592
0.85	High Similarity	NPC83351
0.85	High Similarity	NPC167891
0.8471	Intermediate Similarity	NPC476948
0.8452	Intermediate Similarity	NPC274448
0.8375	Intermediate Similarity	NPC91594
0.8353	Intermediate Similarity	NPC255143
0.8333	Intermediate Similarity	NPC470077
0.8333	Intermediate Similarity	NPC83702
0.8333	Intermediate Similarity	NPC288970
0.8333	Intermediate Similarity	NPC130665
0.8315	Intermediate Similarity	NPC65402
0.8315	Intermediate Similarity	NPC127718
0.8313	Intermediate Similarity	NPC87489
0.8313	Intermediate Similarity	NPC155521
0.8276	Intermediate Similarity	NPC49783
0.8276	Intermediate Similarity	NPC115607
0.8272	Intermediate Similarity	NPC137587
0.8256	Intermediate Similarity	NPC149224
0.8235	Intermediate Similarity	NPC477578
0.8235	Intermediate Similarity	NPC35933
0.8235	Intermediate Similarity	NPC157257
0.8228	Intermediate Similarity	NPC476366
0.8228	Intermediate Similarity	NPC201048
0.8222	Intermediate Similarity	NPC8774
0.8205	Intermediate Similarity	NPC110799
0.8193	Intermediate Similarity	NPC476646
0.8182	Intermediate Similarity	NPC295668
0.8182	Intermediate Similarity	NPC473893
0.8182	Intermediate Similarity	NPC471560
0.8148	Intermediate Similarity	NPC470711
0.8148	Intermediate Similarity	NPC470758
0.8132	Intermediate Similarity	NPC98457
0.8132	Intermediate Similarity	NPC227583
0.8132	Intermediate Similarity	NPC12103
0.8125	Intermediate Similarity	NPC69383
0.8125	Intermediate Similarity	NPC171148
0.8125	Intermediate Similarity	NPC313179
0.8125	Intermediate Similarity	NPC477923
0.8125	Intermediate Similarity	NPC66566
0.8118	Intermediate Similarity	NPC231310
0.8118	Intermediate Similarity	NPC238485
0.8101	Intermediate Similarity	NPC265485
0.8101	Intermediate Similarity	NPC220939
0.8095	Intermediate Similarity	NPC49964
0.8095	Intermediate Similarity	NPC470049
0.8095	Intermediate Similarity	NPC304285
0.809	Intermediate Similarity	NPC471453
0.8077	Intermediate Similarity	NPC34834
0.8072	Intermediate Similarity	NPC96362
0.8068	Intermediate Similarity	NPC246028
0.8068	Intermediate Similarity	NPC97103
0.8049	Intermediate Similarity	NPC476314
0.8043	Intermediate Similarity	NPC261807
0.8025	Intermediate Similarity	NPC470749
0.8023	Intermediate Similarity	NPC266511
0.8	Intermediate Similarity	NPC474634
0.8	Intermediate Similarity	NPC23748
0.8	Intermediate Similarity	NPC477138
0.8	Intermediate Similarity	NPC317458
0.8	Intermediate Similarity	NPC310013
0.8	Intermediate Similarity	NPC470558
0.8	Intermediate Similarity	NPC49208
0.8	Intermediate Similarity	NPC243342
0.7978	Intermediate Similarity	NPC329596
0.7978	Intermediate Similarity	NPC204188
0.7978	Intermediate Similarity	NPC291484
0.7978	Intermediate Similarity	NPC80561
0.7978	Intermediate Similarity	NPC3345
0.7978	Intermediate Similarity	NPC11216
0.7976	Intermediate Similarity	NPC249423
0.7976	Intermediate Similarity	NPC474752
0.7976	Intermediate Similarity	NPC6707
0.7976	Intermediate Similarity	NPC264245
0.7976	Intermediate Similarity	NPC7505
0.7976	Intermediate Similarity	NPC474683
0.7976	Intermediate Similarity	NPC82986
0.7976	Intermediate Similarity	NPC474731
0.7976	Intermediate Similarity	NPC474759
0.7975	Intermediate Similarity	NPC471268
0.7975	Intermediate Similarity	NPC242992
0.7975	Intermediate Similarity	NPC471271
0.7975	Intermediate Similarity	NPC23954
0.7975	Intermediate Similarity	NPC167706
0.7955	Intermediate Similarity	NPC133588
0.7955	Intermediate Similarity	NPC280556
0.7952	Intermediate Similarity	NPC72755
0.7952	Intermediate Similarity	NPC476367
0.7935	Intermediate Similarity	NPC57664
0.7935	Intermediate Similarity	NPC72204
0.7931	Intermediate Similarity	NPC261266
0.7927	Intermediate Similarity	NPC477427
0.7927	Intermediate Similarity	NPC471798
0.7927	Intermediate Similarity	NPC477426
0.7927	Intermediate Similarity	NPC474826
0.7927	Intermediate Similarity	NPC477425
0.7927	Intermediate Similarity	NPC477924
0.7922	Intermediate Similarity	NPC114651
0.7907	Intermediate Similarity	NPC46320
0.7907	Intermediate Similarity	NPC15534
0.7907	Intermediate Similarity	NPC205845
0.7907	Intermediate Similarity	NPC185568
0.7901	Intermediate Similarity	NPC291503
0.7901	Intermediate Similarity	NPC32832
0.7895	Intermediate Similarity	NPC287339
0.7889	Intermediate Similarity	NPC41554
0.7889	Intermediate Similarity	NPC97404
0.7889	Intermediate Similarity	NPC477574
0.7882	Intermediate Similarity	NPC202389
0.7882	Intermediate Similarity	NPC218616
0.7882	Intermediate Similarity	NPC296701
0.7875	Intermediate Similarity	NPC182717
0.7875	Intermediate Similarity	NPC471799
0.7865	Intermediate Similarity	NPC470361
0.7857	Intermediate Similarity	NPC22403
0.7857	Intermediate Similarity	NPC209944
0.7857	Intermediate Similarity	NPC287749
0.7857	Intermediate Similarity	NPC234193
0.7857	Intermediate Similarity	NPC295131
0.7857	Intermediate Similarity	NPC164840
0.7857	Intermediate Similarity	NPC241290
0.7848	Intermediate Similarity	NPC92801
0.7831	Intermediate Similarity	NPC275910
0.7831	Intermediate Similarity	NPC11908
0.7821	Intermediate Similarity	NPC96484
0.7821	Intermediate Similarity	NPC208999
0.7816	Intermediate Similarity	NPC290731
0.7805	Intermediate Similarity	NPC477925
0.7805	Intermediate Similarity	NPC274079
0.7805	Intermediate Similarity	NPC253190
0.7805	Intermediate Similarity	NPC106432
0.7802	Intermediate Similarity	NPC53555
0.7802	Intermediate Similarity	NPC137461
0.7802	Intermediate Similarity	NPC307776
0.7792	Intermediate Similarity	NPC267027
0.7792	Intermediate Similarity	NPC326310
0.7791	Intermediate Similarity	NPC470384
0.7791	Intermediate Similarity	NPC475789
0.7791	Intermediate Similarity	NPC132635
0.7778	Intermediate Similarity	NPC471797
0.7778	Intermediate Similarity	NPC306727
0.7778	Intermediate Similarity	NPC91858
0.7765	Intermediate Similarity	NPC25554
0.7765	Intermediate Similarity	NPC474531
0.7765	Intermediate Similarity	NPC47761
0.7753	Intermediate Similarity	NPC474668
0.7753	Intermediate Similarity	NPC471952
0.775	Intermediate Similarity	NPC164022
0.775	Intermediate Similarity	NPC471272
0.775	Intermediate Similarity	NPC242001
0.775	Intermediate Similarity	NPC477792
0.7742	Intermediate Similarity	NPC210717
0.7742	Intermediate Similarity	NPC103165
0.7738	Intermediate Similarity	NPC291379
0.7738	Intermediate Similarity	NPC47982
0.7738	Intermediate Similarity	NPC242767
0.7738	Intermediate Similarity	NPC209430
0.7738	Intermediate Similarity	NPC30986
0.7738	Intermediate Similarity	NPC28862
0.7738	Intermediate Similarity	NPC84694
0.7738	Intermediate Similarity	NPC328714
0.7738	Intermediate Similarity	NPC143182
0.7738	Intermediate Similarity	NPC109546
0.7738	Intermediate Similarity	NPC81306
0.7727	Intermediate Similarity	NPC175145
0.7727	Intermediate Similarity	NPC476217
0.7727	Intermediate Similarity	NPC475069
0.7727	Intermediate Similarity	NPC6391
0.7727	Intermediate Similarity	NPC125399
0.7722	Intermediate Similarity	NPC9942
0.7717	Intermediate Similarity	NPC472416
0.7717	Intermediate Similarity	NPC472360
0.7717	Intermediate Similarity	NPC144202
0.7711	Intermediate Similarity	NPC214570
0.7711	Intermediate Similarity	NPC130136
0.7711	Intermediate Similarity	NPC169994
0.7701	Intermediate Similarity	NPC474047
0.7684	Intermediate Similarity	NPC38855
0.7684	Intermediate Similarity	NPC473510
0.7674	Intermediate Similarity	NPC101462
0.7674	Intermediate Similarity	NPC50964
0.7674	Intermediate Similarity	NPC30166
0.7674	Intermediate Similarity	NPC7988
0.7667	Intermediate Similarity	NPC477917
0.7667	Intermediate Similarity	NPC82876
0.766	Intermediate Similarity	NPC210337
0.766	Intermediate Similarity	NPC473244
0.7647	Intermediate Similarity	NPC233332
0.7647	Intermediate Similarity	NPC236112
0.7647	Intermediate Similarity	NPC13554
0.764	Intermediate Similarity	NPC233744
0.764	Intermediate Similarity	NPC189777
0.764	Intermediate Similarity	NPC166857
0.764	Intermediate Similarity	NPC470620

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 NPC471408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	2051
0.2-0.3	3827
0.3-0.4	2177
0.4-0.5	672
0.5-0.6	187
0.6-0.7	61
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD8264	Approved
0.7529	Intermediate Similarity	NPD7645	Phase 2
0.7262	Intermediate Similarity	NPD7339	Approved
0.7262	Intermediate Similarity	NPD6942	Approved
0.7241	Intermediate Similarity	NPD7525	Registered
0.7216	Intermediate Similarity	NPD4225	Approved
0.7176	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6933	Approved
0.7071	Intermediate Similarity	NPD4159	Approved
0.7065	Intermediate Similarity	NPD7524	Approved
0.7065	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD368	Approved
0.7045	Intermediate Similarity	NPD4748	Discontinued
0.7011	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7115	Discovery
0.6941	Remote Similarity	NPD6926	Approved
0.6941	Remote Similarity	NPD6924	Approved
0.69	Remote Similarity	NPD5344	Discontinued
0.6854	Remote Similarity	NPD6930	Phase 2
0.6854	Remote Similarity	NPD7514	Phase 3
0.6854	Remote Similarity	NPD6931	Approved
0.6854	Remote Similarity	NPD7332	Phase 2
0.6813	Remote Similarity	NPD6695	Phase 3
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD7639	Approved
0.6744	Remote Similarity	NPD4784	Approved
0.6744	Remote Similarity	NPD4785	Approved
0.6742	Remote Similarity	NPD6929	Approved
0.6739	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4786	Approved
0.6706	Remote Similarity	NPD7151	Approved
0.6706	Remote Similarity	NPD7152	Approved
0.6706	Remote Similarity	NPD7150	Approved
0.6703	Remote Similarity	NPD3667	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6629	Remote Similarity	NPD7145	Approved
0.6598	Remote Similarity	NPD6079	Approved
0.6596	Remote Similarity	NPD3618	Phase 1
0.6593	Remote Similarity	NPD6902	Approved
0.6588	Remote Similarity	NPD7144	Approved
0.6588	Remote Similarity	NPD7143	Approved
0.6562	Remote Similarity	NPD5328	Approved
0.6531	Remote Similarity	NPD5778	Approved
0.6531	Remote Similarity	NPD5779	Approved
0.6526	Remote Similarity	NPD7750	Discontinued
0.6517	Remote Similarity	NPD6925	Approved
0.6517	Remote Similarity	NPD6932	Approved
0.6517	Remote Similarity	NPD5776	Phase 2
0.6512	Remote Similarity	NPD4243	Approved
0.6494	Remote Similarity	NPD342	Phase 1
0.6489	Remote Similarity	NPD1696	Phase 3
0.6489	Remote Similarity	NPD6893	Approved
0.6471	Remote Similarity	NPD6648	Approved
0.6471	Remote Similarity	NPD6923	Approved
0.6471	Remote Similarity	NPD6922	Approved
0.6449	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD7515	Phase 2
0.6413	Remote Similarity	NPD6898	Phase 1
0.6392	Remote Similarity	NPD6051	Approved
0.6383	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4202	Approved
0.6346	Remote Similarity	NPD7632	Discontinued
0.6346	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD1694	Approved
0.6304	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7748	Approved
0.6283	Remote Similarity	NPD7328	Approved
0.6283	Remote Similarity	NPD7327	Approved
0.6279	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7087	Discontinued
0.6261	Remote Similarity	NPD8033	Approved
0.6261	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.6228	Remote Similarity	NPD7516	Approved
0.6226	Remote Similarity	NPD5141	Approved
0.6224	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6101	Approved
0.6211	Remote Similarity	NPD3666	Approved
0.6211	Remote Similarity	NPD3665	Phase 1
0.6211	Remote Similarity	NPD3133	Approved
0.6204	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4219	Approved
0.62	Remote Similarity	NPD6399	Phase 3
0.6196	Remote Similarity	NPD4195	Approved
0.6196	Remote Similarity	NPD6683	Phase 2
0.6176	Remote Similarity	NPD5221	Approved
0.6176	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5222	Approved
0.6174	Remote Similarity	NPD8294	Approved
0.6174	Remote Similarity	NPD8377	Approved
0.6168	Remote Similarity	NPD6640	Phase 3
0.6162	Remote Similarity	NPD7838	Discovery
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6126	Remote Similarity	NPD8297	Approved
0.6121	Remote Similarity	NPD8378	Approved
0.6121	Remote Similarity	NPD8379	Approved
0.6121	Remote Similarity	NPD8296	Approved
0.6121	Remote Similarity	NPD8380	Approved
0.6121	Remote Similarity	NPD8335	Approved
0.6117	Remote Similarity	NPD5173	Approved
0.6117	Remote Similarity	NPD7902	Approved
0.6117	Remote Similarity	NPD4755	Approved
0.6111	Remote Similarity	NPD4190	Phase 3
0.6111	Remote Similarity	NPD5275	Approved
0.61	Remote Similarity	NPD7637	Suspended
0.6095	Remote Similarity	NPD5223	Approved
0.6091	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5279	Phase 3
0.6071	Remote Similarity	NPD4632	Approved
0.6067	Remote Similarity	NPD4732	Discontinued
0.6058	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5290	Discontinued
0.6055	Remote Similarity	NPD6881	Approved
0.6055	Remote Similarity	NPD6899	Approved
0.6055	Remote Similarity	NPD6686	Approved
0.6042	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD5226	Approved
0.6038	Remote Similarity	NPD4633	Approved
0.6038	Remote Similarity	NPD5224	Approved
0.6038	Remote Similarity	NPD5225	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD4697	Phase 3
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD46	Approved
0.5983	Remote Similarity	NPD8517	Approved
0.5983	Remote Similarity	NPD8516	Approved
0.5983	Remote Similarity	NPD8515	Approved
0.5983	Remote Similarity	NPD8513	Phase 3
0.5981	Remote Similarity	NPD5175	Approved
0.5981	Remote Similarity	NPD5174	Approved
0.5979	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5697	Approved
0.5957	Remote Similarity	NPD4822	Approved
0.5957	Remote Similarity	NPD4820	Approved
0.5957	Remote Similarity	NPD4821	Approved
0.5957	Remote Similarity	NPD4819	Approved
0.5946	Remote Similarity	NPD7102	Approved
0.5946	Remote Similarity	NPD6883	Approved
0.5946	Remote Similarity	NPD4634	Approved
0.5946	Remote Similarity	NPD7290	Approved
0.5938	Remote Similarity	NPD5362	Discontinued
0.5934	Remote Similarity	NPD8039	Approved
0.5918	Remote Similarity	NPD5690	Phase 2
0.5918	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7507	Approved
0.5914	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6011	Approved
0.5909	Remote Similarity	NPD7320	Approved
0.59	Remote Similarity	NPD4753	Phase 2
0.5893	Remote Similarity	NPD6617	Approved
0.5893	Remote Similarity	NPD6847	Approved
0.5893	Remote Similarity	NPD8130	Phase 1
0.5893	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6869	Approved
0.5893	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD371	Approved
0.5859	Remote Similarity	NPD3573	Approved
0.5856	Remote Similarity	NPD6013	Approved
0.5856	Remote Similarity	NPD6372	Approved
0.5856	Remote Similarity	NPD6014	Approved
0.5856	Remote Similarity	NPD6012	Approved
0.5856	Remote Similarity	NPD6373	Approved
0.5842	Remote Similarity	NPD3168	Discontinued
0.5842	Remote Similarity	NPD7136	Phase 2
0.5841	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4223	Phase 3
0.5833	Remote Similarity	NPD4754	Approved
0.5825	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6412	Phase 2
0.5818	Remote Similarity	NPD5701	Approved
0.5816	Remote Similarity	NPD5329	Approved
0.581	Remote Similarity	NPD6084	Phase 2
0.581	Remote Similarity	NPD6083	Phase 2
0.5804	Remote Similarity	NPD6371	Approved
0.5789	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4695	Discontinued
0.5784	Remote Similarity	NPD7983	Approved
0.5776	Remote Similarity	NPD6009	Approved
0.5773	Remote Similarity	NPD5332	Approved
0.5773	Remote Similarity	NPD5331	Approved
0.5773	Remote Similarity	NPD6110	Phase 1
0.5773	Remote Similarity	NPD7154	Phase 3
0.5772	Remote Similarity	NPD7319	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