NPASS Compound

Structure

NPC265515 OpenBabel07101718332D 40 45 0 0 0 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 -5.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -3.4641 -3.0000 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 -1.7321 -4.0000 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 -1.7321 -3.0000 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 -2.5981 -4.5000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 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 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 21 2 0 0 0 0 12 22 2 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 26 1 0 0 0 0 17 33 1 0 0 0 0 18 34 1 0 0 0 0 19 35 2 0 0 0 0 19 37 1 0 0 0 0 20 36 2 0 0 0 0 20 38 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 29 2 0 0 0 0 26 28 1 0 0 0 0 26 30 2 0 0 0 0 27 28 1 0 0 0 0 27 31 2 0 0 0 0 28 32 2 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 37 1 0 0 0 0 32 38 1 0 0 0 0 33 39 1 0 0 0 0 34 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.2
Volume:	561.112
LogP:	7.67
LogD:	5.132
LogS:	-4.056
# Rotatable Bonds:	5
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	3.29
Fsp3:	0.235
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.507
MDCK Permeability:	1.5675621398258954e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.774
20% Bioavailability (F20%):	0.682
30% Bioavailability (F30%):	0.101

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	101.25267791748047%
Volume Distribution (VD):	0.583
Pgp-substrate:	1.333030343055725%

ADMET: Metabolism

CYP1A2-inhibitor:	0.35
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.82
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.574
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	1.422
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.482
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.364
Carcinogencity:	0.833
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC265515

Natural Product ID:	NPC265515
*Common Name:**	2,2,2',2'-Tetramethyl-2H,2'h-5,5'-Bibenzo[H]Chromene-6,6'-Diyl Diacetate
IUPAC Name:	[5-(6-acetyloxy-2,2-dimethylbenzo[h]chromen-5-yl)-2,2-dimethylbenzo[h]chromen-6-yl] acetate
Synonyms:
Standard InCHIKey:	HJRRQKPSQNLHCK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C34H30O6/c1-19(35)37-31-23-13-9-7-11-21(23)29-25(15-17-33(3,4)39-29)27(31)28-26-16-18-34(5,6)40-30(26)22-12-8-10-14-24(22)32(28)38-20(2)36/h7-18H,1-6H3
SMILES:	CC(=O)Oc1c2ccccc2c2c(C=CC(C)(C)O2)c1c1c2C=CC(C)(C)Oc2c2ccccc2c1OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481076
PubChem CID:	13871797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO4592	Lippia sidoides	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421746]
NPO4592	Lippia sidoides	Species	Verbenaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[476985]
NPT1577	Cell Line	SW1573	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[476985]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[476985]

☑ 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 NPC265515 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	430
0.1-0.2	1825
0.2-0.3	4321
0.3-0.4	12415
0.4-0.5	6294
0.5-0.6	6467
0.6-0.7	9779
0.7-0.8	1136
0.8-0.85	28
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9104	High Similarity	NPC71372
0.8473	Intermediate Similarity	NPC212559
0.837	Intermediate Similarity	NPC128321
0.8346	Intermediate Similarity	NPC473464
0.8346	Intermediate Similarity	NPC476332
0.8175	Intermediate Similarity	NPC156298
0.8151	Intermediate Similarity	NPC36732
0.8125	Intermediate Similarity	NPC476191
0.8088	Intermediate Similarity	NPC61685
0.8085	Intermediate Similarity	NPC472524
0.8069	Intermediate Similarity	NPC472523
0.8042	Intermediate Similarity	NPC115861
0.803	Intermediate Similarity	NPC238075
0.8029	Intermediate Similarity	NPC133407
0.8029	Intermediate Similarity	NPC28476
0.8015	Intermediate Similarity	NPC283169
0.8014	Intermediate Similarity	NPC19157
0.7986	Intermediate Similarity	NPC472646
0.7986	Intermediate Similarity	NPC176590
0.7986	Intermediate Similarity	NPC71465
0.7947	Intermediate Similarity	NPC118000
0.7947	Intermediate Similarity	NPC205501
0.7947	Intermediate Similarity	NPC162976
0.7931	Intermediate Similarity	NPC265335
0.7917	Intermediate Similarity	NPC472647
0.7917	Intermediate Similarity	NPC472648
0.7917	Intermediate Similarity	NPC133463
0.7917	Intermediate Similarity	NPC206525
0.7917	Intermediate Similarity	NPC191462
0.7917	Intermediate Similarity	NPC472649
0.7917	Intermediate Similarity	NPC170328
0.7891	Intermediate Similarity	NPC186033
0.7887	Intermediate Similarity	NPC469956
0.7881	Intermediate Similarity	NPC474107
0.7877	Intermediate Similarity	NPC79372
0.7877	Intermediate Similarity	NPC273623
0.7868	Intermediate Similarity	NPC475839
0.7857	Intermediate Similarity	NPC81261
0.7852	Intermediate Similarity	NPC125617
0.7847	Intermediate Similarity	NPC37410
0.7847	Intermediate Similarity	NPC258780
0.7832	Intermediate Similarity	NPC469952
0.7832	Intermediate Similarity	NPC469955
0.7817	Intermediate Similarity	NPC191395
0.781	Intermediate Similarity	NPC302211
0.7801	Intermediate Similarity	NPC16577
0.7786	Intermediate Similarity	NPC280760
0.777	Intermediate Similarity	NPC279118
0.7761	Intermediate Similarity	NPC25648
0.7748	Intermediate Similarity	NPC60389
0.7748	Intermediate Similarity	NPC170239
0.7748	Intermediate Similarity	NPC97937
0.7748	Intermediate Similarity	NPC275125
0.7746	Intermediate Similarity	NPC249425
0.7742	Intermediate Similarity	NPC477691
0.774	Intermediate Similarity	NPC474530
0.774	Intermediate Similarity	NPC474540
0.774	Intermediate Similarity	NPC474521
0.773	Intermediate Similarity	NPC47288
0.7708	Intermediate Similarity	NPC211352
0.7707	Intermediate Similarity	NPC36077
0.7698	Intermediate Similarity	NPC291899
0.7698	Intermediate Similarity	NPC248557
0.7692	Intermediate Similarity	NPC292385
0.7692	Intermediate Similarity	NPC282508
0.7692	Intermediate Similarity	NPC125709
0.7692	Intermediate Similarity	NPC160623
0.7682	Intermediate Similarity	NPC475872
0.7682	Intermediate Similarity	NPC471608
0.7677	Intermediate Similarity	NPC477690
0.7676	Intermediate Similarity	NPC96719
0.7676	Intermediate Similarity	NPC222108
0.7671	Intermediate Similarity	NPC286843
0.7667	Intermediate Similarity	NPC474599
0.7667	Intermediate Similarity	NPC472840
0.7664	Intermediate Similarity	NPC45663
0.7664	Intermediate Similarity	NPC322569
0.7658	Intermediate Similarity	NPC36354
0.7655	Intermediate Similarity	NPC474600
0.7655	Intermediate Similarity	NPC184269
0.7655	Intermediate Similarity	NPC131950
0.7647	Intermediate Similarity	NPC98748
0.7647	Intermediate Similarity	NPC113790
0.7643	Intermediate Similarity	NPC232387
0.7639	Intermediate Similarity	NPC469611
0.7639	Intermediate Similarity	NPC303144
0.7639	Intermediate Similarity	NPC189482
0.7635	Intermediate Similarity	NPC61783
0.7635	Intermediate Similarity	NPC20520
0.7632	Intermediate Similarity	NPC211565
0.7622	Intermediate Similarity	NPC11089
0.7622	Intermediate Similarity	NPC254000
0.7619	Intermediate Similarity	NPC476171
0.7619	Intermediate Similarity	NPC306365
0.7616	Intermediate Similarity	NPC475719
0.7616	Intermediate Similarity	NPC43716
0.7616	Intermediate Similarity	NPC101255
0.7616	Intermediate Similarity	NPC86069
0.761	Intermediate Similarity	NPC312993
0.7609	Intermediate Similarity	NPC48623
0.7609	Intermediate Similarity	NPC168707
0.7606	Intermediate Similarity	NPC474616
0.7603	Intermediate Similarity	NPC234865
0.7593	Intermediate Similarity	NPC30027
0.7589	Intermediate Similarity	NPC163248
0.7589	Intermediate Similarity	NPC101894
0.7586	Intermediate Similarity	NPC469610
0.7584	Intermediate Similarity	NPC472791
0.7584	Intermediate Similarity	NPC472792
0.7574	Intermediate Similarity	NPC139047
0.7571	Intermediate Similarity	NPC474237
0.7569	Intermediate Similarity	NPC149337
0.7569	Intermediate Similarity	NPC472590
0.7569	Intermediate Similarity	NPC153019
0.7569	Intermediate Similarity	NPC8899
0.7569	Intermediate Similarity	NPC471983
0.7568	Intermediate Similarity	NPC270256
0.7568	Intermediate Similarity	NPC24635
0.7568	Intermediate Similarity	NPC35501
0.7568	Intermediate Similarity	NPC278600
0.7568	Intermediate Similarity	NPC144512
0.7568	Intermediate Similarity	NPC137262
0.7568	Intermediate Similarity	NPC47040
0.7568	Intermediate Similarity	NPC37428
0.7562	Intermediate Similarity	NPC273467
0.7562	Intermediate Similarity	NPC189552
0.7561	Intermediate Similarity	NPC313304
0.7551	Intermediate Similarity	NPC474610
0.7551	Intermediate Similarity	NPC167517
0.7547	Intermediate Similarity	NPC177650
0.7537	Intermediate Similarity	NPC87563
0.7536	Intermediate Similarity	NPC129176
0.7535	Intermediate Similarity	NPC289316
0.7535	Intermediate Similarity	NPC474821
0.7535	Intermediate Similarity	NPC142087
0.7535	Intermediate Similarity	NPC46978
0.7535	Intermediate Similarity	NPC95034
0.7534	Intermediate Similarity	NPC141023
0.7534	Intermediate Similarity	NPC184677
0.7534	Intermediate Similarity	NPC147030
0.7518	Intermediate Similarity	NPC170749
0.7518	Intermediate Similarity	NPC471449
0.7518	Intermediate Similarity	NPC249836
0.7518	Intermediate Similarity	NPC320847
0.7517	Intermediate Similarity	NPC289624
0.7517	Intermediate Similarity	NPC27578
0.7517	Intermediate Similarity	NPC473049
0.7517	Intermediate Similarity	NPC73656
0.7517	Intermediate Similarity	NPC472794
0.7516	Intermediate Similarity	NPC174251
0.7516	Intermediate Similarity	NPC174311
0.7516	Intermediate Similarity	NPC192258
0.7516	Intermediate Similarity	NPC153182
0.7516	Intermediate Similarity	NPC476200
0.7516	Intermediate Similarity	NPC268484
0.75	Intermediate Similarity	NPC196193
0.75	Intermediate Similarity	NPC315807
0.75	Intermediate Similarity	NPC471498
0.75	Intermediate Similarity	NPC473048
0.75	Intermediate Similarity	NPC50720
0.75	Intermediate Similarity	NPC471542
0.75	Intermediate Similarity	NPC474617
0.75	Intermediate Similarity	NPC169942
0.75	Intermediate Similarity	NPC325003
0.75	Intermediate Similarity	NPC248786
0.75	Intermediate Similarity	NPC471503
0.75	Intermediate Similarity	NPC143725
0.75	Intermediate Similarity	NPC32463
0.75	Intermediate Similarity	NPC186325
0.7484	Intermediate Similarity	NPC300983
0.7483	Intermediate Similarity	NPC293642
0.7483	Intermediate Similarity	NPC181675
0.7483	Intermediate Similarity	NPC60704
0.7483	Intermediate Similarity	NPC258083
0.7483	Intermediate Similarity	NPC215300
0.7483	Intermediate Similarity	NPC139595
0.7483	Intermediate Similarity	NPC474636
0.7483	Intermediate Similarity	NPC38017
0.7481	Intermediate Similarity	NPC473718
0.7468	Intermediate Similarity	NPC142863
0.7467	Intermediate Similarity	NPC138149
0.7466	Intermediate Similarity	NPC471910
0.7466	Intermediate Similarity	NPC296624
0.7466	Intermediate Similarity	NPC470406
0.7466	Intermediate Similarity	NPC472522
0.7466	Intermediate Similarity	NPC138940
0.7466	Intermediate Similarity	NPC167111
0.7466	Intermediate Similarity	NPC318400
0.7466	Intermediate Similarity	NPC133956
0.7466	Intermediate Similarity	NPC207002
0.7466	Intermediate Similarity	NPC77196
0.7465	Intermediate Similarity	NPC474632
0.7465	Intermediate Similarity	NPC471826
0.7465	Intermediate Similarity	NPC329272
0.7464	Intermediate Similarity	NPC14177
0.7464	Intermediate Similarity	NPC103916
0.7452	Intermediate Similarity	NPC476154
0.7452	Intermediate Similarity	NPC223720
0.7452	Intermediate Similarity	NPC115203
0.7451	Intermediate Similarity	NPC274454

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 NPC265515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	1053
0.2-0.3	1427
0.3-0.4	2895
0.4-0.5	1836
0.5-0.6	1069
0.6-0.7	454
0.7-0.8	53
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8692	High Similarity	NPD1611	Approved
0.803	Intermediate Similarity	NPD7644	Approved
0.7801	Intermediate Similarity	NPD4625	Phase 3
0.7652	Intermediate Similarity	NPD5535	Approved
0.7647	Intermediate Similarity	NPD5691	Approved
0.7571	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD7985	Registered
0.7484	Intermediate Similarity	NPD3226	Approved
0.7464	Intermediate Similarity	NPD4626	Approved
0.745	Intermediate Similarity	NPD2346	Discontinued
0.7448	Intermediate Similarity	NPD8032	Phase 2
0.7397	Intermediate Similarity	NPD2979	Phase 3
0.7397	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7379	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1281	Approved
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD17	Approved
0.7338	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1398	Phase 1
0.7303	Intermediate Similarity	NPD7003	Approved
0.7299	Intermediate Similarity	NPD7340	Approved
0.7296	Intermediate Similarity	NPD8455	Phase 2
0.7292	Intermediate Similarity	NPD2237	Approved
0.7286	Intermediate Similarity	NPD3496	Discontinued
0.7279	Intermediate Similarity	NPD4140	Approved
0.7266	Intermediate Similarity	NPD1651	Approved
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5124	Phase 1
0.723	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7177	Discontinued
0.7226	Intermediate Similarity	NPD6671	Approved
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7203	Intermediate Similarity	NPD1283	Approved
0.7203	Intermediate Similarity	NPD3225	Approved
0.72	Intermediate Similarity	NPD3748	Approved
0.7192	Intermediate Similarity	NPD7095	Approved
0.7183	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2861	Phase 2
0.7168	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.7153	Intermediate Similarity	NPD2797	Approved
0.7153	Intermediate Similarity	NPD3266	Approved
0.7153	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD5585	Approved
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7133	Intermediate Similarity	NPD4749	Approved
0.7132	Intermediate Similarity	NPD7635	Approved
0.7123	Intermediate Similarity	NPD4908	Phase 1
0.7099	Intermediate Similarity	NPD7768	Phase 2
0.7092	Intermediate Similarity	NPD1778	Approved
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8312	Approved
0.7076	Intermediate Similarity	NPD8313	Approved
0.7051	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2531	Phase 2
0.7039	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD2438	Suspended
0.7039	Intermediate Similarity	NPD5405	Approved
0.7039	Intermediate Similarity	NPD5404	Approved
0.7039	Intermediate Similarity	NPD5406	Approved
0.7027	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD3268	Approved
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7015	Intermediate Similarity	NPD2342	Discontinued
0.7014	Intermediate Similarity	NPD5327	Phase 3
0.7013	Intermediate Similarity	NPD6674	Discontinued
0.7013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9697	Approved
0.6988	Remote Similarity	NPD7229	Phase 3
0.6975	Remote Similarity	NPD7819	Suspended
0.6974	Remote Similarity	NPD7033	Discontinued
0.6974	Remote Similarity	NPD4308	Phase 3
0.6968	Remote Similarity	NPD3750	Approved
0.6962	Remote Similarity	NPD2675	Approved
0.6962	Remote Similarity	NPD2676	Approved
0.6962	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD498	Approved
0.6957	Remote Similarity	NPD495	Approved
0.6957	Remote Similarity	NPD496	Approved
0.6937	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD6099	Approved
0.6913	Remote Similarity	NPD6798	Discontinued
0.6913	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD497	Approved
0.6905	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4359	Approved
0.6897	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6232	Discontinued
0.6883	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD422	Phase 1
0.6867	Remote Similarity	NPD6233	Phase 2
0.6859	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD709	Approved
0.6857	Remote Similarity	NPD6387	Discontinued
0.6849	Remote Similarity	NPD8651	Approved
0.6848	Remote Similarity	NPD3749	Approved
0.6842	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD8127	Discontinued
0.6821	Remote Similarity	NPD7549	Discontinued
0.6818	Remote Similarity	NPD4477	Approved
0.6818	Remote Similarity	NPD4476	Approved
0.6818	Remote Similarity	NPD2935	Discontinued
0.68	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3787	Discontinued
0.6783	Remote Similarity	NPD3444	Approved
0.6783	Remote Similarity	NPD3443	Approved
0.6783	Remote Similarity	NPD3445	Approved
0.6774	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6004	Phase 3
0.6774	Remote Similarity	NPD6002	Phase 3
0.6774	Remote Similarity	NPD6005	Phase 3
0.6774	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6666	Approved
0.6772	Remote Similarity	NPD6667	Approved
0.6768	Remote Similarity	NPD5929	Approved
0.6765	Remote Similarity	NPD7473	Discontinued
0.6755	Remote Similarity	NPD4475	Approved
0.6755	Remote Similarity	NPD4474	Approved
0.6753	Remote Similarity	NPD2799	Discontinued
0.675	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2897	Discontinued
0.6727	Remote Similarity	NPD5402	Approved
0.6714	Remote Similarity	NPD5283	Phase 1
0.671	Remote Similarity	NPD6032	Approved
0.6708	Remote Similarity	NPD7427	Discontinued
0.6707	Remote Similarity	NPD5709	Phase 3
0.6705	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3764	Approved
0.6689	Remote Similarity	NPD7294	Phase 1
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4618	Approved
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD6746	Phase 2
0.6667	Remote Similarity	NPD8285	Discontinued
0.6667	Remote Similarity	NPD4622	Approved
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6090	Discontinued
0.6646	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD4628	Phase 3
0.6645	Remote Similarity	NPD4870	Approved
0.6644	Remote Similarity	NPD1610	Phase 2
0.6644	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3705	Approved
0.6644	Remote Similarity	NPD1535	Discovery
0.6644	Remote Similarity	NPD4624	Approved
0.6627	Remote Similarity	NPD7199	Phase 2
0.6626	Remote Similarity	NPD7458	Discontinued
0.6625	Remote Similarity	NPD7390	Discontinued
0.6624	Remote Similarity	NPD7037	Approved
0.6623	Remote Similarity	NPD4097	Suspended
0.6623	Remote Similarity	NPD6353	Approved
0.6608	Remote Similarity	NPD4481	Phase 3
0.6606	Remote Similarity	NPD37	Approved
0.66	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1481	Phase 2
0.6597	Remote Similarity	NPD1548	Phase 1
0.6587	Remote Similarity	NPD4966	Approved
0.6587	Remote Similarity	NPD4967	Phase 2
0.6587	Remote Similarity	NPD4965	Approved
0.6584	Remote Similarity	NPD2533	Approved
0.6584	Remote Similarity	NPD2534	Approved
0.6584	Remote Similarity	NPD2532	Approved
0.6584	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1243	Approved
0.6581	Remote Similarity	NPD5688	Approved
0.6581	Remote Similarity	NPD5689	Approved
0.6579	Remote Similarity	NPD1296	Phase 2
0.6571	Remote Similarity	NPD1139	Approved
0.6571	Remote Similarity	NPD1137	Approved
0.6569	Remote Similarity	NPD968	Approved
0.6568	Remote Similarity	NPD5494	Approved
0.6564	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4340	Discontinued
0.6554	Remote Similarity	NPD1669	Approved
0.655	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7783	Phase 2
0.6543	Remote Similarity	NPD4319	Phase 2
0.6541	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7466	Approved
0.6538	Remote Similarity	NPD4108	Discontinued
0.6533	Remote Similarity	NPD6584	Phase 3
0.6533	Remote Similarity	NPD2798	Approved
0.6527	Remote Similarity	NPD5616	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