NPASS Compound

Structure

NPC208120 OpenBabel07101718282D 26 29 0 0 1 0 0 0 0 0999 V2000 5.1369 1.0000 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 -2.7321 0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 1 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 -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 0.5000 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 -0.0000 2.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 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 0.0000 0.0000 C 0 0 0 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 1 1 6 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 10 21 2 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 23 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.14
Volume:	439.261
LogP:	4.026
LogD:	3.266
LogS:	-4.247
# Rotatable Bonds:	5
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	3.573
Fsp3:	0.16
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:	-5.314
MDCK Permeability:	6.943348125787452e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	98.66993713378906%
Volume Distribution (VD):	0.629
Pgp-substrate:	1.2788970470428467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.849
CYP1A2-substrate:	0.397
CYP2C19-inhibitor:	0.35
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.825
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.706
CYP2D6-substrate:	0.516
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	10.597
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.19
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.948
Carcinogencity:	0.271
Eye Corrosion:	0.003
Eye Irritation:	0.799
Respiratory Toxicity:	0.179

Download Data

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

Natural Product: NPC208120

Natural Product ID:	NPC208120
*Common Name:**	Teuvincenone A
IUPAC Name:	(9S,11bR)-5,7,11-trihydroxy-4,4,9,11b-tetramethyl-1,2,8,9-tetrahydronaphtho[2,1-f][1]benzofuran-3,6-dione
Synonyms:
Standard InCHIKey:	GWRKJHSVPDIUPU-FFVOIRBGSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-8-7-9-13(22)11-12(15(24)17(9)26-8)20(4)6-5-10(21)19(2,3)18(20)16(25)14(11)23/h8,22,24-25H,5-7H2,1-4H3/t8-,20+/m0/s1
SMILES:	C[C@H]1Cc2c(O1)c(O)c1c(c2O)C(=O)C(=C2[C@]1(C)CCC(=O)C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1287906
PubChem CID:	14467636
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21084196]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24239	Teucrium polium	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	7
Others	1

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	30000.0	nM	PMID[572042]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3500.0	nM	PMID[572042]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	2700.0	nM	PMID[572042]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	1500.0	nM	PMID[572042]
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	>	30000.0	nM	PMID[572042]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[572043]
NPT1	Others	Radical scavenging activity		IC50	=	63000.0	nM	PMID[572041]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	50.0	%	PMID[572041]

☑ 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 NPC208120 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	434
0.1-0.2	1883
0.2-0.3	3871
0.3-0.4	9541
0.4-0.5	9243
0.5-0.6	4427
0.6-0.7	5810
0.7-0.8	5958
0.8-0.85	1282
0.85-0.9	212
0.9-0.95	21
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173587
0.9935	High Similarity	NPC21016
0.9935	High Similarity	NPC146584
0.9809	High Similarity	NPC232936
0.9747	High Similarity	NPC213416
0.9618	High Similarity	NPC475055
0.9557	High Similarity	NPC102372
0.9371	High Similarity	NPC29055
0.9231	High Similarity	NPC273248
0.9167	High Similarity	NPC161778
0.9114	High Similarity	NPC25850
0.9114	High Similarity	NPC276815
0.9107	High Similarity	NPC228209
0.9074	High Similarity	NPC473286
0.9074	High Similarity	NPC326520
0.9057	High Similarity	NPC283301
0.9042	High Similarity	NPC23553
0.9042	High Similarity	NPC77179
0.9018	High Similarity	NPC170245
0.9006	High Similarity	NPC65746
0.8994	High Similarity	NPC8927
0.8947	High Similarity	NPC240808
0.8929	High Similarity	NPC221820
0.8896	High Similarity	NPC473313
0.8896	High Similarity	NPC220313
0.8896	High Similarity	NPC18100
0.8896	High Similarity	NPC472278
0.8896	High Similarity	NPC329669
0.8896	High Similarity	NPC197168
0.8896	High Similarity	NPC475985
0.8896	High Similarity	NPC205265
0.8896	High Similarity	NPC472281
0.8896	High Similarity	NPC476822
0.8896	High Similarity	NPC270837
0.8896	High Similarity	NPC236132
0.8889	High Similarity	NPC187354
0.8882	High Similarity	NPC246153
0.8855	High Similarity	NPC472276
0.8855	High Similarity	NPC315306
0.8855	High Similarity	NPC313717
0.8848	High Similarity	NPC45760
0.8841	High Similarity	NPC25361
0.8841	High Similarity	NPC472277
0.8834	High Similarity	NPC294965
0.8834	High Similarity	NPC470694
0.8834	High Similarity	NPC81679
0.8827	High Similarity	NPC14353
0.8827	High Similarity	NPC56085
0.8827	High Similarity	NPC228785
0.8795	High Similarity	NPC165456
0.8788	High Similarity	NPC472452
0.878	High Similarity	NPC7483
0.878	High Similarity	NPC41301
0.8773	High Similarity	NPC40491
0.8773	High Similarity	NPC32694
0.8773	High Similarity	NPC61010
0.8773	High Similarity	NPC278052
0.8773	High Similarity	NPC66288
0.8773	High Similarity	NPC474186
0.8772	High Similarity	NPC240508
0.8772	High Similarity	NPC182693
0.8765	High Similarity	NPC95936
0.8765	High Similarity	NPC100123
0.8765	High Similarity	NPC250214
0.8765	High Similarity	NPC85121
0.875	High Similarity	NPC470942
0.8735	High Similarity	NPC6588
0.8735	High Similarity	NPC477154
0.8735	High Similarity	NPC126204
0.8735	High Similarity	NPC117854
0.8727	High Similarity	NPC316262
0.8727	High Similarity	NPC314653
0.8727	High Similarity	NPC470457
0.8727	High Similarity	NPC475888
0.872	High Similarity	NPC211107
0.8712	High Similarity	NPC313368
0.8712	High Similarity	NPC476283
0.8712	High Similarity	NPC155302
0.8712	High Similarity	NPC45146
0.8712	High Similarity	NPC475886
0.8712	High Similarity	NPC470810
0.8712	High Similarity	NPC320359
0.8712	High Similarity	NPC246478
0.8712	High Similarity	NPC235018
0.8712	High Similarity	NPC80375
0.8712	High Similarity	NPC161947
0.8712	High Similarity	NPC474287
0.8712	High Similarity	NPC36217
0.8712	High Similarity	NPC119224
0.8706	High Similarity	NPC246877
0.8704	High Similarity	NPC223787
0.8704	High Similarity	NPC241904
0.8704	High Similarity	NPC165977
0.8704	High Similarity	NPC300727
0.8704	High Similarity	NPC217677
0.8698	High Similarity	NPC245975
0.8688	High Similarity	NPC218628
0.8683	High Similarity	NPC152477
0.8683	High Similarity	NPC288813
0.8683	High Similarity	NPC475805
0.8683	High Similarity	NPC242395
0.8675	High Similarity	NPC43319
0.8675	High Similarity	NPC37870
0.8667	High Similarity	NPC236521
0.8667	High Similarity	NPC273959
0.8667	High Similarity	NPC248638
0.8667	High Similarity	NPC474240
0.8667	High Similarity	NPC470459
0.8667	High Similarity	NPC152659
0.8659	High Similarity	NPC474351
0.8659	High Similarity	NPC87431
0.8659	High Similarity	NPC474187
0.8659	High Similarity	NPC475883
0.8659	High Similarity	NPC117985
0.8655	High Similarity	NPC476273
0.865	High Similarity	NPC235448
0.865	High Similarity	NPC476242
0.865	High Similarity	NPC329091
0.8647	High Similarity	NPC478050
0.8647	High Similarity	NPC49667
0.8647	High Similarity	NPC8127
0.8642	High Similarity	NPC274730
0.8642	High Similarity	NPC142339
0.8631	High Similarity	NPC101107
0.8623	High Similarity	NPC474024
0.8623	High Similarity	NPC150131
0.8623	High Similarity	NPC218226
0.8623	High Similarity	NPC158761
0.8623	High Similarity	NPC470456
0.8621	High Similarity	NPC174486
0.8614	High Similarity	NPC62261
0.8614	High Similarity	NPC224280
0.8614	High Similarity	NPC472450
0.8614	High Similarity	NPC275780
0.8614	High Similarity	NPC239752
0.8608	High Similarity	NPC251188
0.8606	High Similarity	NPC215612
0.8606	High Similarity	NPC472402
0.8606	High Similarity	NPC25152
0.8606	High Similarity	NPC201800
0.8598	High Similarity	NPC84571
0.8598	High Similarity	NPC263449
0.8598	High Similarity	NPC287328
0.8598	High Similarity	NPC470326
0.8598	High Similarity	NPC282009
0.8598	High Similarity	NPC472624
0.8589	High Similarity	NPC180011
0.8589	High Similarity	NPC219867
0.8589	High Similarity	NPC475267
0.8589	High Similarity	NPC236796
0.8589	High Similarity	NPC78225
0.8589	High Similarity	NPC474836
0.8589	High Similarity	NPC162869
0.8589	High Similarity	NPC179732
0.8589	High Similarity	NPC156057
0.8589	High Similarity	NPC79053
0.8589	High Similarity	NPC48208
0.8589	High Similarity	NPC469584
0.8589	High Similarity	NPC474208
0.8589	High Similarity	NPC262286
0.8589	High Similarity	NPC36852
0.8588	High Similarity	NPC287243
0.8588	High Similarity	NPC314020
0.8588	High Similarity	NPC227906
0.858	High Similarity	NPC200761
0.858	High Similarity	NPC45849
0.858	High Similarity	NPC158226
0.858	High Similarity	NPC121333
0.858	High Similarity	NPC477503
0.858	High Similarity	NPC470327
0.8571	High Similarity	NPC38469
0.8571	High Similarity	NPC165979
0.8571	High Similarity	NPC163130
0.8571	High Similarity	NPC247136
0.8571	High Similarity	NPC326877
0.8571	High Similarity	NPC177480
0.8571	High Similarity	NPC476637
0.8563	High Similarity	NPC477517
0.8563	High Similarity	NPC470462
0.8563	High Similarity	NPC39091
0.8562	High Similarity	NPC50269
0.8555	High Similarity	NPC475656
0.8555	High Similarity	NPC475148
0.8554	High Similarity	NPC133065
0.8554	High Similarity	NPC189473
0.8554	High Similarity	NPC186686
0.8554	High Similarity	NPC303460
0.8554	High Similarity	NPC124038
0.8554	High Similarity	NPC306321
0.8554	High Similarity	NPC23298
0.8554	High Similarity	NPC249181
0.8554	High Similarity	NPC207690
0.8554	High Similarity	NPC146134
0.8545	High Similarity	NPC472275
0.8545	High Similarity	NPC266314
0.8545	High Similarity	NPC308992
0.8545	High Similarity	NPC278427
0.8545	High Similarity	NPC474239
0.8545	High Similarity	NPC311740
0.8545	High Similarity	NPC471499

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 NPC208120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	1130
0.2-0.3	2227
0.3-0.4	2606
0.4-0.5	1689
0.5-0.6	726
0.6-0.7	291
0.7-0.8	100
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8415	Intermediate Similarity	NPD3882	Suspended
0.8405	Intermediate Similarity	NPD2801	Approved
0.8405	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1934	Approved
0.828	Intermediate Similarity	NPD2800	Approved
0.8263	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD2532	Approved
0.825	Intermediate Similarity	NPD2534	Approved
0.825	Intermediate Similarity	NPD2533	Approved
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.8081	Intermediate Similarity	NPD3818	Discontinued
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7975	Intermediate Similarity	NPD1512	Approved
0.7955	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD1511	Approved
0.7824	Intermediate Similarity	NPD7075	Discontinued
0.7791	Intermediate Similarity	NPD1247	Approved
0.7785	Intermediate Similarity	NPD6651	Approved
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7765	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD7251	Discontinued
0.7692	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7684	Intermediate Similarity	NPD7472	Approved
0.7679	Intermediate Similarity	NPD4380	Phase 2
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD1465	Phase 2
0.7644	Intermediate Similarity	NPD5711	Approved
0.7644	Intermediate Similarity	NPD5710	Approved
0.7598	Intermediate Similarity	NPD6559	Discontinued
0.7572	Intermediate Similarity	NPD6234	Discontinued
0.7542	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD919	Approved
0.7439	Intermediate Similarity	NPD1549	Phase 2
0.7432	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6799	Approved
0.7414	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD37	Approved
0.7381	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4965	Approved
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7317	Intermediate Similarity	NPD2796	Approved
0.7303	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1510	Phase 2
0.7256	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.724	Intermediate Similarity	NPD6782	Approved
0.724	Intermediate Similarity	NPD6781	Approved
0.724	Intermediate Similarity	NPD6777	Approved
0.724	Intermediate Similarity	NPD6778	Approved
0.724	Intermediate Similarity	NPD6779	Approved
0.724	Intermediate Similarity	NPD6776	Approved
0.724	Intermediate Similarity	NPD6780	Approved
0.7239	Intermediate Similarity	NPD1607	Approved
0.7225	Intermediate Similarity	NPD7411	Suspended
0.7216	Intermediate Similarity	NPD3749	Approved
0.7209	Intermediate Similarity	NPD3226	Approved
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7191	Intermediate Similarity	NPD7199	Phase 2
0.7176	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7157	Intermediate Similarity	NPD7907	Approved
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4111	Phase 1
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD4665	Approved
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7118	Intermediate Similarity	NPD7390	Discontinued
0.7117	Intermediate Similarity	NPD1240	Approved
0.7117	Intermediate Similarity	NPD943	Approved
0.7113	Intermediate Similarity	NPD2493	Approved
0.7113	Intermediate Similarity	NPD2494	Approved
0.7108	Intermediate Similarity	NPD2935	Discontinued
0.7093	Intermediate Similarity	NPD5403	Approved
0.7093	Intermediate Similarity	NPD920	Approved
0.7073	Intermediate Similarity	NPD230	Phase 1
0.7072	Intermediate Similarity	NPD2403	Approved
0.7072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6535	Approved
0.7068	Intermediate Similarity	NPD6534	Approved
0.7062	Intermediate Similarity	NPD7768	Phase 2
0.7043	Intermediate Similarity	NPD8312	Approved
0.7043	Intermediate Similarity	NPD8313	Approved
0.7041	Intermediate Similarity	NPD7696	Phase 3
0.7041	Intermediate Similarity	NPD7698	Approved
0.7041	Intermediate Similarity	NPD7697	Approved
0.7026	Intermediate Similarity	NPD3452	Approved
0.7026	Intermediate Similarity	NPD3450	Approved
0.7012	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1613	Approved
0.7005	Intermediate Similarity	NPD4583	Approved
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD4582	Approved
0.6994	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7701	Phase 2
0.6982	Remote Similarity	NPD6674	Discontinued
0.6977	Remote Similarity	NPD5401	Approved
0.6959	Remote Similarity	NPD7699	Phase 2
0.6959	Remote Similarity	NPD7700	Phase 2
0.6954	Remote Similarity	NPD4004	Approved
0.6954	Remote Similarity	NPD4002	Approved
0.695	Remote Similarity	NPD8151	Discontinued
0.6933	Remote Similarity	NPD3027	Phase 3
0.6915	Remote Similarity	NPD7874	Approved
0.6915	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD2488	Approved
0.6911	Remote Similarity	NPD2490	Approved
0.6907	Remote Similarity	NPD2974	Approved
0.6907	Remote Similarity	NPD2973	Approved
0.6907	Remote Similarity	NPD2975	Approved
0.6905	Remote Similarity	NPD1551	Phase 2
0.6901	Remote Similarity	NPD6190	Approved
0.6882	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1243	Approved
0.6881	Remote Similarity	NPD7783	Phase 2
0.6881	Remote Similarity	NPD7801	Approved
0.6881	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7229	Phase 3
0.6867	Remote Similarity	NPD447	Suspended
0.6865	Remote Similarity	NPD7286	Phase 2
0.6864	Remote Similarity	NPD2344	Approved
0.6857	Remote Similarity	NPD1653	Approved
0.6854	Remote Similarity	NPD5761	Phase 2
0.6854	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD7240	Approved
0.6845	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6696	Suspended
0.6821	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3057	Approved
0.6818	Remote Similarity	NPD6823	Phase 2
0.6818	Remote Similarity	NPD2491	Approved
0.6813	Remote Similarity	NPD8127	Discontinued
0.6802	Remote Similarity	NPD4580	Approved
0.6791	Remote Similarity	NPD5953	Discontinued
0.6788	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7985	Registered
0.6765	Remote Similarity	NPD1471	Phase 3
0.6763	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2799	Discontinued
0.6746	Remote Similarity	NPD8366	Approved
0.6737	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3533	Approved
0.6734	Remote Similarity	NPD3448	Approved
0.6734	Remote Similarity	NPD2972	Approved
0.6727	Remote Similarity	NPD4625	Phase 3
0.6723	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7458	Discontinued
0.6707	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD9494	Approved
0.6707	Remote Similarity	NPD4060	Phase 1
0.6707	Remote Similarity	NPD3620	Phase 2
0.6705	Remote Similarity	NPD2309	Approved
0.6687	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2313	Discontinued
0.6684	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6213	Phase 3
0.6667	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD6214	Clinical (unspecified phase)

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