NPASS Compound

Structure

NPC263754 OpenBabel07101718182D 22 23 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 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 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -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 3.4641 -2.0000 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 3.4641 -3.0000 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 -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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 15 18 2 0 0 0 0 16 18 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.16
Volume:	327.983
LogP:	5.528
LogD:	4.344
LogS:	-3.854
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.658
Synthetic Accessibility Score:	3.048
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.706
MDCK Permeability:	2.3609482013853267e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.698

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	99.63556671142578%
Volume Distribution (VD):	0.699
Pgp-substrate:	1.9193323850631714%

ADMET: Metabolism

CYP1A2-inhibitor:	0.324
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.55
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	5.868
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.934
Drug-inuced Liver Injury (DILI):	0.587
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.378
Skin Sensitization:	0.53
Carcinogencity:	0.703
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.438

Download Data

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

Natural Product: NPC263754

Natural Product ID:	NPC263754
*Common Name:**	(Z)-2,2-Dimethyl-8-(3-Methyl-2-Butenyl)-Benzopyran-6-Propenoic Acid
IUPAC Name:	(Z)-3-[2,2-dimethyl-8-(3-methylbut-2-enyl)chromen-6-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	ZKUFWHYBAKVWMB-VURMDHGXSA-N
Standard InCHI:	InChI=1S/C19H22O3/c1-13(2)5-7-15-11-14(6-8-17(20)21)12-16-9-10-19(3,4)22-18(15)16/h5-6,8-12H,7H2,1-4H3,(H,20,21)/b8-6-
SMILES:	CC(=CCc1cc(/C=CC(=O)O)cc2C=CC(C)(C)Oc12)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496045
PubChem CID:	9948201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34000.0	nM	PMID[478521]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10000.0	nM	PMID[478521]

☑ 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 NPC263754 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	252
0.1-0.2	1638
0.2-0.3	4327
0.3-0.4	11668
0.4-0.5	6633
0.5-0.6	6003
0.6-0.7	10042
0.7-0.8	2046
0.8-0.85	60
0.85-0.9	24
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC183154
0.9189	High Similarity	NPC199462
0.9009	High Similarity	NPC473809
0.8992	High Similarity	NPC89630
0.8926	High Similarity	NPC473993
0.8926	High Similarity	NPC243688
0.8862	High Similarity	NPC86774
0.8862	High Similarity	NPC327457
0.8833	High Similarity	NPC291899
0.8772	High Similarity	NPC90903
0.876	High Similarity	NPC93219
0.876	High Similarity	NPC244495
0.8707	High Similarity	NPC33717
0.8699	High Similarity	NPC185066
0.8678	High Similarity	NPC73413
0.8678	High Similarity	NPC201667
0.8667	High Similarity	NPC248429
0.8667	High Similarity	NPC96286
0.8618	High Similarity	NPC37512
0.8618	High Similarity	NPC142087
0.8618	High Similarity	NPC95034
0.8607	High Similarity	NPC202594
0.8607	High Similarity	NPC232692
0.8595	High Similarity	NPC472518
0.8595	High Similarity	NPC109675
0.8595	High Similarity	NPC273772
0.8584	High Similarity	NPC75272
0.8584	High Similarity	NPC471954
0.8571	High Similarity	NPC157473
0.8571	High Similarity	NPC151530
0.8571	High Similarity	NPC474874
0.856	High Similarity	NPC32463
0.8559	High Similarity	NPC227255
0.8559	High Similarity	NPC243677
0.8559	High Similarity	NPC139891
0.8548	High Similarity	NPC2401
0.8525	High Similarity	NPC27671
0.8525	High Similarity	NPC111347
0.8512	High Similarity	NPC13007
0.8512	High Similarity	NPC302211
0.8512	High Similarity	NPC257188
0.8509	High Similarity	NPC141068
0.8504	High Similarity	NPC31849
0.8487	Intermediate Similarity	NPC264976
0.8482	Intermediate Similarity	NPC176971
0.848	Intermediate Similarity	NPC473019
0.8468	Intermediate Similarity	NPC2518
0.8455	Intermediate Similarity	NPC471828
0.8455	Intermediate Similarity	NPC471827
0.8443	Intermediate Similarity	NPC50720
0.8438	Intermediate Similarity	NPC131950
0.843	Intermediate Similarity	NPC52247
0.8417	Intermediate Similarity	NPC31314
0.8417	Intermediate Similarity	NPC193193
0.8413	Intermediate Similarity	NPC109778
0.84	Intermediate Similarity	NPC472519
0.84	Intermediate Similarity	NPC157212
0.8393	Intermediate Similarity	NPC303141
0.8393	Intermediate Similarity	NPC128730
0.8393	Intermediate Similarity	NPC473855
0.8387	Intermediate Similarity	NPC471826
0.8376	Intermediate Similarity	NPC161696
0.8362	Intermediate Similarity	NPC266116
0.8361	Intermediate Similarity	NPC150214
0.8347	Intermediate Similarity	NPC131868
0.8347	Intermediate Similarity	NPC180006
0.8347	Intermediate Similarity	NPC235190
0.8346	Intermediate Similarity	NPC37009
0.8346	Intermediate Similarity	NPC66430
0.8333	Intermediate Similarity	NPC168710
0.8333	Intermediate Similarity	NPC470039
0.8321	Intermediate Similarity	NPC151946
0.8321	Intermediate Similarity	NPC211110
0.8321	Intermediate Similarity	NPC279573
0.832	Intermediate Similarity	NPC224774
0.832	Intermediate Similarity	NPC121104
0.832	Intermediate Similarity	NPC121740
0.832	Intermediate Similarity	NPC258567
0.8319	Intermediate Similarity	NPC326447
0.8308	Intermediate Similarity	NPC26954
0.8308	Intermediate Similarity	NPC38099
0.8306	Intermediate Similarity	NPC165556
0.8305	Intermediate Similarity	NPC473718
0.8305	Intermediate Similarity	NPC296526
0.8304	Intermediate Similarity	NPC109637
0.8295	Intermediate Similarity	NPC180716
0.8295	Intermediate Similarity	NPC326600
0.8295	Intermediate Similarity	NPC50896
0.8295	Intermediate Similarity	NPC62366
0.8295	Intermediate Similarity	NPC204353
0.8295	Intermediate Similarity	NPC213173
0.8295	Intermediate Similarity	NPC224475
0.8293	Intermediate Similarity	NPC290605
0.8293	Intermediate Similarity	NPC154176
0.8293	Intermediate Similarity	NPC143725
0.8293	Intermediate Similarity	NPC173350
0.8288	Intermediate Similarity	NPC307425
0.8281	Intermediate Similarity	NPC194277
0.8281	Intermediate Similarity	NPC329427
0.8281	Intermediate Similarity	NPC14248
0.8281	Intermediate Similarity	NPC317601
0.8279	Intermediate Similarity	NPC144418
0.8279	Intermediate Similarity	NPC251259
0.8279	Intermediate Similarity	NPC187868
0.8268	Intermediate Similarity	NPC80170
0.8268	Intermediate Similarity	NPC113098
0.8264	Intermediate Similarity	NPC14177
0.8264	Intermediate Similarity	NPC247553
0.8261	Intermediate Similarity	NPC149545
0.8254	Intermediate Similarity	NPC469453
0.8254	Intermediate Similarity	NPC81261
0.825	Intermediate Similarity	NPC265547
0.825	Intermediate Similarity	NPC96705
0.825	Intermediate Similarity	NPC152306
0.8244	Intermediate Similarity	NPC155963
0.824	Intermediate Similarity	NPC188327
0.824	Intermediate Similarity	NPC163248
0.824	Intermediate Similarity	NPC234109
0.8235	Intermediate Similarity	NPC163398
0.8231	Intermediate Similarity	NPC472525
0.823	Intermediate Similarity	NPC473393
0.8226	Intermediate Similarity	NPC474237
0.8226	Intermediate Similarity	NPC147896
0.822	Intermediate Similarity	NPC87563
0.8217	Intermediate Similarity	NPC7526
0.8217	Intermediate Similarity	NPC163557
0.8217	Intermediate Similarity	NPC167111
0.8217	Intermediate Similarity	NPC296624
0.8217	Intermediate Similarity	NPC83535
0.8217	Intermediate Similarity	NPC1220
0.8217	Intermediate Similarity	NPC318400
0.8217	Intermediate Similarity	NPC141822
0.8217	Intermediate Similarity	NPC207002
0.8217	Intermediate Similarity	NPC291551
0.8217	Intermediate Similarity	NPC133956
0.8217	Intermediate Similarity	NPC471910
0.8217	Intermediate Similarity	NPC205797
0.8217	Intermediate Similarity	NPC241165
0.8217	Intermediate Similarity	NPC222036
0.8217	Intermediate Similarity	NPC142563
0.8214	Intermediate Similarity	NPC179686
0.8214	Intermediate Similarity	NPC470202
0.8203	Intermediate Similarity	NPC29734
0.8203	Intermediate Similarity	NPC267336
0.8203	Intermediate Similarity	NPC272650
0.8198	Intermediate Similarity	NPC107101
0.8197	Intermediate Similarity	NPC302107
0.8197	Intermediate Similarity	NPC163200
0.8195	Intermediate Similarity	NPC152771
0.8195	Intermediate Similarity	NPC195357
0.8189	Intermediate Similarity	NPC474289
0.8182	Intermediate Similarity	NPC37428
0.8182	Intermediate Similarity	NPC298796
0.8182	Intermediate Similarity	NPC144512
0.8182	Intermediate Similarity	NPC137262
0.8182	Intermediate Similarity	NPC47040
0.8182	Intermediate Similarity	NPC98748
0.8182	Intermediate Similarity	NPC281356
0.8182	Intermediate Similarity	NPC35501
0.8182	Intermediate Similarity	NPC278600
0.8175	Intermediate Similarity	NPC289316
0.816	Intermediate Similarity	NPC168259
0.8154	Intermediate Similarity	NPC267412
0.8154	Intermediate Similarity	NPC74655
0.8154	Intermediate Similarity	NPC473054
0.8154	Intermediate Similarity	NPC100986
0.8154	Intermediate Similarity	NPC253574
0.8154	Intermediate Similarity	NPC164269
0.8154	Intermediate Similarity	NPC166672
0.8154	Intermediate Similarity	NPC47163
0.8154	Intermediate Similarity	NPC84894
0.8154	Intermediate Similarity	NPC198381
0.8154	Intermediate Similarity	NPC195343
0.8154	Intermediate Similarity	NPC319859
0.8154	Intermediate Similarity	NPC287182
0.8154	Intermediate Similarity	NPC127888
0.8154	Intermediate Similarity	NPC55149
0.8154	Intermediate Similarity	NPC98179
0.8154	Intermediate Similarity	NPC18804
0.8154	Intermediate Similarity	NPC260265
0.8154	Intermediate Similarity	NPC307412
0.8151	Intermediate Similarity	NPC51345
0.8145	Intermediate Similarity	NPC315807
0.814	Intermediate Similarity	NPC469956
0.8136	Intermediate Similarity	NPC141003
0.8136	Intermediate Similarity	NPC35344
0.813	Intermediate Similarity	NPC476165
0.8125	Intermediate Similarity	NPC475102
0.812	Intermediate Similarity	NPC473988
0.812	Intermediate Similarity	NPC71903
0.812	Intermediate Similarity	NPC312881
0.811	Intermediate Similarity	NPC293642
0.811	Intermediate Similarity	NPC139595
0.811	Intermediate Similarity	NPC478215
0.811	Intermediate Similarity	NPC60704
0.811	Intermediate Similarity	NPC199204
0.8106	Intermediate Similarity	NPC281014
0.8106	Intermediate Similarity	NPC225106
0.8106	Intermediate Similarity	NPC294456
0.8106	Intermediate Similarity	NPC153818

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 NPC263754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1058
0.2-0.3	1316
0.3-0.4	2612
0.4-0.5	1958
0.5-0.6	1230
0.6-0.7	589
0.7-0.8	132
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4626	Approved
0.8559	High Similarity	NPD9697	Approved
0.843	Intermediate Similarity	NPD422	Phase 1
0.8362	Intermediate Similarity	NPD5535	Approved
0.8333	Intermediate Similarity	NPD5691	Approved
0.8319	Intermediate Similarity	NPD3134	Approved
0.8306	Intermediate Similarity	NPD2797	Approved
0.8217	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5124	Phase 1
0.8197	Intermediate Similarity	NPD3496	Discontinued
0.8087	Intermediate Similarity	NPD1358	Approved
0.803	Intermediate Similarity	NPD2799	Discontinued
0.8017	Intermediate Similarity	NPD2684	Approved
0.8	Intermediate Similarity	NPD6671	Approved
0.8	Intermediate Similarity	NPD4060	Phase 1
0.7984	Intermediate Similarity	NPD2313	Discontinued
0.7984	Intermediate Similarity	NPD3268	Approved
0.7926	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD1241	Discontinued
0.7805	Intermediate Similarity	NPD1894	Discontinued
0.7795	Intermediate Similarity	NPD3225	Approved
0.7778	Intermediate Similarity	NPD9717	Approved
0.7761	Intermediate Similarity	NPD4308	Phase 3
0.775	Intermediate Similarity	NPD7843	Approved
0.7734	Intermediate Similarity	NPD3267	Approved
0.7734	Intermediate Similarity	NPD3266	Approved
0.771	Intermediate Similarity	NPD6798	Discontinued
0.7704	Intermediate Similarity	NPD2935	Discontinued
0.7698	Intermediate Similarity	NPD1611	Approved
0.7634	Intermediate Similarity	NPD7095	Approved
0.7619	Intermediate Similarity	NPD3847	Discontinued
0.7597	Intermediate Similarity	NPD1203	Approved
0.7594	Intermediate Similarity	NPD4307	Phase 2
0.7589	Intermediate Similarity	NPD5049	Phase 3
0.7581	Intermediate Similarity	NPD7644	Approved
0.7576	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4476	Approved
0.7574	Intermediate Similarity	NPD4477	Approved
0.7561	Intermediate Similarity	NPD7157	Approved
0.7559	Intermediate Similarity	NPD1535	Discovery
0.7557	Intermediate Similarity	NPD6832	Phase 2
0.7557	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7097	Phase 1
0.754	Intermediate Similarity	NPD1778	Approved
0.7538	Intermediate Similarity	NPD2798	Approved
0.7537	Intermediate Similarity	NPD6355	Discontinued
0.7537	Intermediate Similarity	NPD4340	Discontinued
0.752	Intermediate Similarity	NPD1548	Phase 1
0.7518	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2346	Discontinued
0.7518	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1481	Phase 2
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7482	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3750	Approved
0.7482	Intermediate Similarity	NPD7003	Approved
0.7479	Intermediate Similarity	NPD290	Approved
0.7464	Intermediate Similarity	NPD2424	Discontinued
0.7463	Intermediate Similarity	NPD4140	Approved
0.7462	Intermediate Similarity	NPD987	Approved
0.7459	Intermediate Similarity	NPD821	Approved
0.7459	Intermediate Similarity	NPD1138	Approved
0.7444	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1296	Phase 2
0.7442	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6387	Discontinued
0.7405	Intermediate Similarity	NPD3690	Phase 2
0.7405	Intermediate Similarity	NPD3691	Phase 2
0.7398	Intermediate Similarity	NPD1398	Phase 1
0.7395	Intermediate Similarity	NPD968	Approved
0.7385	Intermediate Similarity	NPD1283	Approved
0.7385	Intermediate Similarity	NPD8651	Approved
0.7377	Intermediate Similarity	NPD1137	Approved
0.7377	Intermediate Similarity	NPD1139	Approved
0.7376	Intermediate Similarity	NPD6667	Approved
0.7376	Intermediate Similarity	NPD6666	Approved
0.7372	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD2860	Approved
0.7368	Intermediate Similarity	NPD5163	Phase 2
0.7368	Intermediate Similarity	NPD1809	Phase 2
0.7368	Intermediate Similarity	NPD2859	Approved
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7364	Intermediate Similarity	NPD1608	Approved
0.736	Intermediate Similarity	NPD7340	Approved
0.7357	Intermediate Similarity	NPD4628	Phase 3
0.7355	Intermediate Similarity	NPD5451	Approved
0.7345	Intermediate Similarity	NPD845	Approved
0.7329	Intermediate Similarity	NPD7411	Suspended
0.7323	Intermediate Similarity	NPD5585	Approved
0.7319	Intermediate Similarity	NPD2862	Discontinued
0.7308	Intermediate Similarity	NPD6582	Phase 2
0.7308	Intermediate Similarity	NPD6583	Phase 3
0.7308	Intermediate Similarity	NPD4749	Approved
0.7293	Intermediate Similarity	NPD2614	Approved
0.7293	Intermediate Similarity	NPD4908	Phase 1
0.7287	Intermediate Similarity	NPD1281	Approved
0.7287	Intermediate Similarity	NPD1610	Phase 2
0.7287	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1652	Phase 2
0.7286	Intermediate Similarity	NPD1243	Approved
0.7281	Intermediate Similarity	NPD2934	Approved
0.7281	Intermediate Similarity	NPD2933	Approved
0.728	Intermediate Similarity	NPD2557	Approved
0.7279	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5846	Approved
0.7266	Intermediate Similarity	NPD6002	Phase 3
0.7266	Intermediate Similarity	NPD6004	Phase 3
0.7266	Intermediate Similarity	NPD2344	Approved
0.7266	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6516	Phase 2
0.7266	Intermediate Similarity	NPD6005	Phase 3
0.7266	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD17	Approved
0.7259	Intermediate Similarity	NPD6233	Phase 2
0.7259	Intermediate Similarity	NPD4062	Phase 3
0.7259	Intermediate Similarity	NPD8032	Phase 2
0.7258	Intermediate Similarity	NPD592	Approved
0.7258	Intermediate Similarity	NPD594	Approved
0.7252	Intermediate Similarity	NPD6696	Suspended
0.7244	Intermediate Similarity	NPD9545	Approved
0.7231	Intermediate Similarity	NPD3972	Approved
0.7227	Intermediate Similarity	NPD5909	Discontinued
0.7222	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD3596	Phase 2
0.7218	Intermediate Similarity	NPD2861	Phase 2
0.7203	Intermediate Similarity	NPD6799	Approved
0.7194	Intermediate Similarity	NPD2796	Approved
0.7188	Intermediate Similarity	NPD1651	Approved
0.7185	Intermediate Similarity	NPD411	Approved
0.7183	Intermediate Similarity	NPD2354	Approved
0.7179	Intermediate Similarity	NPD3020	Approved
0.7176	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3685	Discontinued
0.7165	Intermediate Similarity	NPD5536	Phase 2
0.7153	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7133	Intermediate Similarity	NPD7768	Phase 2
0.7132	Intermediate Similarity	NPD2667	Approved
0.7132	Intermediate Similarity	NPD5745	Approved
0.7132	Intermediate Similarity	NPD2668	Approved
0.712	Intermediate Similarity	NPD5283	Phase 1
0.7114	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7819	Suspended
0.7113	Intermediate Similarity	NPD7976	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6581	Approved
0.7109	Intermediate Similarity	NPD6580	Approved
0.7103	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD228	Approved
0.709	Intermediate Similarity	NPD2237	Approved
0.7086	Intermediate Similarity	NPD7075	Discontinued
0.708	Intermediate Similarity	NPD1240	Approved
0.708	Intermediate Similarity	NPD2979	Phase 3
0.708	Intermediate Similarity	NPD2203	Discontinued
0.7075	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7458	Discontinued
0.7075	Intermediate Similarity	NPD3226	Approved
0.7071	Intermediate Similarity	NPD6032	Approved
0.7063	Intermediate Similarity	NPD3887	Approved
0.7063	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1048	Approved
0.7059	Intermediate Similarity	NPD846	Approved
0.7059	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7985	Registered
0.7059	Intermediate Similarity	NPD940	Approved
0.7054	Intermediate Similarity	NPD3445	Approved
0.7054	Intermediate Similarity	NPD3444	Approved
0.7054	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3049	Approved
0.7054	Intermediate Similarity	NPD3443	Approved
0.7045	Intermediate Similarity	NPD4359	Approved
0.7045	Intermediate Similarity	NPD5327	Phase 3
0.7029	Intermediate Similarity	NPD4618	Approved
0.7029	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4622	Approved
0.7029	Intermediate Similarity	NPD1933	Approved
0.7027	Intermediate Similarity	NPD6502	Phase 2
0.7027	Intermediate Similarity	NPD6599	Discontinued
0.7027	Intermediate Similarity	NPD6585	Discontinued
0.7023	Intermediate Similarity	NPD1091	Approved
0.7021	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7440	Discontinued
0.7008	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1876	Approved
0.6986	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5746	Approved
0.6983	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2157	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