NPASS Compound

Structure

NPC87794 OpenBabel07101718292D 22 25 0 0 1 0 0 0 0 0999 V2000 4.3414 -2.5361 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 2.5334 -0.6045 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 1.3578 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 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 1.5388 -0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -2.3271 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 2.9401 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7591 -3.2406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9346 -1.6226 0.0000 O 0 0 0 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 15 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 17 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 6 0 0 0 17 20 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	296.495
LogP:	2.466
LogD:	2.4
LogS:	-3.485
# Rotatable Bonds:	1
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	3.572
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.215
MDCK Permeability:	9.091236279346049e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.641
30% Bioavailability (F30%):	0.676

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	94.97911834716797%
Volume Distribution (VD):	1.284
Pgp-substrate:	5.601900100708008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.844
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.46
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.362
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.522

ADMET: Excretion

Clearance (CL):	14.72
Half-life (T1/2):	0.63

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.145
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.135
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.264
Respiratory Toxicity:	0.623

Download Data

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

Natural Product: NPC87794

Natural Product ID:	NPC87794
*Common Name:**	3'-O-Methylbrazilin
IUPAC Name:	(6aS,11bR)-9-methoxy-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,10-triol
Synonyms:	3'-O-Methylbrazilin
Standard InCHIKey:	RDWWRPSMRUBPHK-DLBZAZTESA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-21-15-4-9-7-17(20)8-22-14-5-10(18)2-3-11(14)16(17)12(9)6-13(15)19/h2-6,16,18-20H,7-8H2,1H3/t16-,17+/m0/s1
SMILES:	COc1cc2C[C@]3(COc4cc(ccc4[C@H]3c2cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2207721
PubChem CID:	13846641
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 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
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[527340]

☑ 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 NPC87794 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	474
0.1-0.2	1729
0.2-0.3	4321
0.3-0.4	11900
0.4-0.5	6491
0.5-0.6	4108
0.6-0.7	7458
0.7-0.8	4835
0.8-0.85	847
0.85-0.9	428
0.9-0.95	98
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC211758
0.9855	High Similarity	NPC44530
0.9855	High Similarity	NPC317237
0.9855	High Similarity	NPC277951
0.9783	High Similarity	NPC274721
0.9783	High Similarity	NPC155392
0.9783	High Similarity	NPC135767
0.942	High Similarity	NPC94994
0.9348	High Similarity	NPC162659
0.9348	High Similarity	NPC265433
0.9348	High Similarity	NPC248727
0.9348	High Similarity	NPC270456
0.9286	High Similarity	NPC184797
0.9286	High Similarity	NPC309124
0.9214	High Similarity	NPC245207
0.9214	High Similarity	NPC236306
0.9214	High Similarity	NPC260741
0.9214	High Similarity	NPC473739
0.9214	High Similarity	NPC70682
0.9214	High Similarity	NPC127218
0.9214	High Similarity	NPC25966
0.9214	High Similarity	NPC232164
0.9214	High Similarity	NPC319647
0.9209	High Similarity	NPC234952
0.9209	High Similarity	NPC230734
0.9209	High Similarity	NPC227503
0.9209	High Similarity	NPC474639
0.9203	High Similarity	NPC317380
0.9161	High Similarity	NPC473108
0.9155	High Similarity	NPC107161
0.9155	High Similarity	NPC59841
0.9155	High Similarity	NPC2613
0.9155	High Similarity	NPC204347
0.9155	High Similarity	NPC475891
0.9143	High Similarity	NPC276490
0.9137	High Similarity	NPC112939
0.9137	High Similarity	NPC474206
0.9137	High Similarity	NPC470356
0.9137	High Similarity	NPC94750
0.9137	High Similarity	NPC121812
0.9137	High Similarity	NPC151224
0.9137	High Similarity	NPC112246
0.9085	High Similarity	NPC247291
0.9085	High Similarity	NPC471389
0.9085	High Similarity	NPC35216
0.9078	High Similarity	NPC32630
0.9071	High Similarity	NPC173660
0.9071	High Similarity	NPC306441
0.9071	High Similarity	NPC16435
0.9071	High Similarity	NPC302701
0.9071	High Similarity	NPC269091
0.9058	High Similarity	NPC127624
0.9058	High Similarity	NPC86655
0.9058	High Similarity	NPC202762
0.9034	High Similarity	NPC233980
0.9028	High Similarity	NPC469795
0.9028	High Similarity	NPC280092
0.9028	High Similarity	NPC45257
0.9028	High Similarity	NPC12641
0.9028	High Similarity	NPC50250
0.9028	High Similarity	NPC93323
0.9014	High Similarity	NPC160283
0.9014	High Similarity	NPC259519
0.9014	High Similarity	NPC254759
0.9014	High Similarity	NPC27495
0.9007	High Similarity	NPC474282
0.9007	High Similarity	NPC103976
0.9007	High Similarity	NPC102904
0.9007	High Similarity	NPC176051
0.9007	High Similarity	NPC211549
0.9007	High Similarity	NPC107551
0.9007	High Similarity	NPC326797
0.9	High Similarity	NPC234333
0.9	High Similarity	NPC195022
0.9	High Similarity	NPC61946
0.9	High Similarity	NPC47398
0.9	High Similarity	NPC260898
0.9	High Similarity	NPC164787
0.8993	High Similarity	NPC229442
0.8993	High Similarity	NPC168059
0.8993	High Similarity	NPC11060
0.8973	High Similarity	NPC21776
0.8973	High Similarity	NPC474397
0.8973	High Similarity	NPC16269
0.8958	High Similarity	NPC102044
0.8958	High Similarity	NPC81638
0.8958	High Similarity	NPC47633
0.8958	High Similarity	NPC85264
0.8951	High Similarity	NPC265075
0.8951	High Similarity	NPC263261
0.8951	High Similarity	NPC87725
0.8944	High Similarity	NPC471388
0.8944	High Similarity	NPC292882
0.8944	High Similarity	NPC184613
0.8929	High Similarity	NPC478085
0.8926	High Similarity	NPC160196
0.8913	High Similarity	NPC126836
0.8912	High Similarity	NPC473876
0.8897	High Similarity	NPC63879
0.8889	High Similarity	NPC277784
0.8881	High Similarity	NPC198038
0.8865	High Similarity	NPC240279
0.8865	High Similarity	NPC214853
0.8865	High Similarity	NPC55239
0.8865	High Similarity	NPC180602
0.8865	High Similarity	NPC313081
0.8865	High Similarity	NPC473413
0.8857	High Similarity	NPC475840
0.8857	High Similarity	NPC263064
0.8857	High Similarity	NPC158331
0.8849	High Similarity	NPC469907
0.8844	High Similarity	NPC101376
0.8836	High Similarity	NPC307466
0.8836	High Similarity	NPC469557
0.8828	High Similarity	NPC474104
0.8828	High Similarity	NPC477616
0.8828	High Similarity	NPC469630
0.8828	High Similarity	NPC173203
0.8828	High Similarity	NPC163508
0.8819	High Similarity	NPC178054
0.8819	High Similarity	NPC71046
0.8819	High Similarity	NPC311530
0.8811	High Similarity	NPC114171
0.8811	High Similarity	NPC6300
0.8811	High Similarity	NPC471183
0.8811	High Similarity	NPC230124
0.8808	High Similarity	NPC188578
0.8808	High Similarity	NPC80918
0.8803	High Similarity	NPC143139
0.8803	High Similarity	NPC472336
0.8803	High Similarity	NPC470802
0.8803	High Similarity	NPC472334
0.8803	High Similarity	NPC133025
0.8803	High Similarity	NPC202846
0.8794	High Similarity	NPC209199
0.8794	High Similarity	NPC188378
0.8794	High Similarity	NPC206737
0.8794	High Similarity	NPC106215
0.8794	High Similarity	NPC276026
0.8794	High Similarity	NPC555
0.8794	High Similarity	NPC170694
0.8794	High Similarity	NPC287745
0.8794	High Similarity	NPC7515
0.8794	High Similarity	NPC56764
0.8794	High Similarity	NPC469659
0.8794	High Similarity	NPC289258
0.8786	High Similarity	NPC253105
0.8786	High Similarity	NPC204215
0.8786	High Similarity	NPC61477
0.8786	High Similarity	NPC78770
0.8786	High Similarity	NPC126029
0.8786	High Similarity	NPC219876
0.8786	High Similarity	NPC261619
0.8786	High Similarity	NPC185604
0.8786	High Similarity	NPC201587
0.8786	High Similarity	NPC15658
0.8786	High Similarity	NPC175067
0.8786	High Similarity	NPC6451
0.8784	High Similarity	NPC329836
0.8777	High Similarity	NPC91291
0.8776	High Similarity	NPC324492
0.8776	High Similarity	NPC317053
0.8776	High Similarity	NPC260397
0.8776	High Similarity	NPC112251
0.8768	High Similarity	NPC226331
0.8768	High Similarity	NPC46274
0.8767	High Similarity	NPC304894
0.8767	High Similarity	NPC473845
0.8767	High Similarity	NPC15659
0.8759	High Similarity	NPC470917
0.875	High Similarity	NPC109240
0.875	High Similarity	NPC22317
0.875	High Similarity	NPC266197
0.875	High Similarity	NPC234568
0.875	High Similarity	NPC291101
0.8741	High Similarity	NPC301765
0.8741	High Similarity	NPC156948
0.8741	High Similarity	NPC477938
0.8741	High Similarity	NPC35550
0.8741	High Similarity	NPC86605
0.8741	High Similarity	NPC3072
0.8741	High Similarity	NPC46277
0.8733	High Similarity	NPC2745
0.8732	High Similarity	NPC10314
0.8732	High Similarity	NPC472337
0.8732	High Similarity	NPC108198
0.8732	High Similarity	NPC126409
0.8732	High Similarity	NPC134968
0.8732	High Similarity	NPC99572
0.8732	High Similarity	NPC200557
0.8732	High Similarity	NPC158142
0.8732	High Similarity	NPC69029
0.8732	High Similarity	NPC294884
0.8725	High Similarity	NPC476969
0.8723	High Similarity	NPC36661
0.8723	High Similarity	NPC32778
0.8716	High Similarity	NPC327412
0.8716	High Similarity	NPC320970
0.8716	High Similarity	NPC328567
0.8716	High Similarity	NPC320671

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 NPC87794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	936
0.2-0.3	1887
0.3-0.4	2743
0.4-0.5	1586
0.5-0.6	884
0.6-0.7	592
0.7-0.8	107
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8786	High Similarity	NPD1612	Clinical (unspecified phase)
0.8786	High Similarity	NPD1613	Approved
0.8768	High Similarity	NPD1529	Clinical (unspecified phase)
0.8696	High Similarity	NPD1530	Clinical (unspecified phase)
0.8571	High Similarity	NPD3027	Phase 3
0.8369	Intermediate Similarity	NPD4908	Phase 1
0.8298	Intermediate Similarity	NPD2861	Phase 2
0.8261	Intermediate Similarity	NPD1610	Phase 2
0.8252	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4625	Phase 3
0.8138	Intermediate Similarity	NPD3620	Phase 2
0.8138	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7199	Phase 2
0.8025	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1934	Approved
0.8014	Intermediate Similarity	NPD4749	Approved
0.7888	Intermediate Similarity	NPD6234	Discontinued
0.7877	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7815	Intermediate Similarity	NPD5762	Approved
0.7815	Intermediate Similarity	NPD5763	Approved
0.7778	Intermediate Similarity	NPD3892	Phase 2
0.777	Intermediate Similarity	NPD4060	Phase 1
0.775	Intermediate Similarity	NPD2801	Approved
0.7718	Intermediate Similarity	NPD5735	Approved
0.7712	Intermediate Similarity	NPD6674	Discontinued
0.7712	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD37	Approved
0.7671	Intermediate Similarity	NPD3018	Phase 2
0.7665	Intermediate Similarity	NPD7228	Approved
0.7658	Intermediate Similarity	NPD1653	Approved
0.7654	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4965	Approved
0.7654	Intermediate Similarity	NPD3882	Suspended
0.7654	Intermediate Similarity	NPD4966	Approved
0.7654	Intermediate Similarity	NPD4967	Phase 2
0.7651	Intermediate Similarity	NPD6166	Phase 2
0.7651	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5283	Phase 1
0.755	Intermediate Similarity	NPD6353	Approved
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.7517	Intermediate Similarity	NPD2983	Phase 2
0.7517	Intermediate Similarity	NPD5327	Phase 3
0.7517	Intermediate Similarity	NPD2982	Phase 2
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD1511	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD3705	Approved
0.7483	Intermediate Similarity	NPD4624	Approved
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7468	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD228	Approved
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.7421	Intermediate Similarity	NPD1512	Approved
0.7417	Intermediate Similarity	NPD4140	Approved
0.7415	Intermediate Similarity	NPD3094	Phase 2
0.7412	Intermediate Similarity	NPD7054	Approved
0.741	Intermediate Similarity	NPD5494	Approved
0.7397	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3817	Phase 2
0.7376	Intermediate Similarity	NPD6671	Approved
0.7368	Intermediate Similarity	NPD7472	Approved
0.7368	Intermediate Similarity	NPD3657	Discovery
0.7365	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8054	Approved
0.7356	Intermediate Similarity	NPD8053	Approved
0.7341	Intermediate Similarity	NPD7549	Discontinued
0.7321	Intermediate Similarity	NPD6232	Discontinued
0.7319	Intermediate Similarity	NPD3022	Approved
0.7319	Intermediate Similarity	NPD3021	Approved
0.7314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1558	Phase 1
0.7299	Intermediate Similarity	NPD4578	Approved
0.7299	Intermediate Similarity	NPD7311	Approved
0.7299	Intermediate Similarity	NPD4577	Approved
0.7299	Intermediate Similarity	NPD7312	Approved
0.7299	Intermediate Similarity	NPD7313	Approved
0.7299	Intermediate Similarity	NPD7310	Approved
0.7294	Intermediate Similarity	NPD7473	Discontinued
0.7285	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4005	Discontinued
0.7283	Intermediate Similarity	NPD7685	Pre-registration
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4663	Approved
0.726	Intermediate Similarity	NPD1091	Approved
0.726	Intermediate Similarity	NPD3092	Approved
0.7257	Intermediate Similarity	NPD7309	Approved
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD5124	Phase 1
0.7255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7447	Phase 1
0.7239	Intermediate Similarity	NPD4678	Approved
0.7239	Intermediate Similarity	NPD4675	Approved
0.7235	Intermediate Similarity	NPD2489	Approved
0.7235	Intermediate Similarity	NPD27	Approved
0.7232	Intermediate Similarity	NPD7906	Approved
0.723	Intermediate Similarity	NPD6696	Suspended
0.723	Intermediate Similarity	NPD8651	Approved
0.7226	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6797	Phase 2
0.7215	Intermediate Similarity	NPD7466	Approved
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6331	Phase 2
0.7215	Intermediate Similarity	NPD3750	Approved
0.7212	Intermediate Similarity	NPD7819	Suspended
0.7208	Intermediate Similarity	NPD6653	Approved
0.7188	Intermediate Similarity	NPD7213	Phase 3
0.7188	Intermediate Similarity	NPD7212	Phase 2
0.7186	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7831	Phase 2
0.7186	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7833	Phase 2
0.7184	Intermediate Similarity	NPD7251	Discontinued
0.7184	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD2969	Approved
0.7176	Intermediate Similarity	NPD2970	Approved
0.717	Intermediate Similarity	NPD2677	Approved
0.7161	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4538	Approved
0.7161	Intermediate Similarity	NPD4536	Approved
0.716	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD5177	Phase 3
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1375	Discontinued
0.7134	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3540	Phase 1
0.7134	Intermediate Similarity	NPD7266	Discontinued
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD7157	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5058	Phase 3
0.7122	Intermediate Similarity	NPD2684	Approved
0.7118	Intermediate Similarity	NPD7229	Phase 3
0.7118	Intermediate Similarity	NPD3051	Approved
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD5588	Approved
0.7108	Intermediate Similarity	NPD5929	Approved
0.7107	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD3091	Approved
0.7099	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2157	Approved
0.7089	Intermediate Similarity	NPD1549	Phase 2
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7083	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2238	Phase 2
0.7073	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3539	Phase 1
0.7066	Intermediate Similarity	NPD2563	Approved
0.7066	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2560	Approved
0.7062	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6959	Discontinued
0.7042	Intermediate Similarity	NPD7843	Approved
0.7037	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7028	Phase 2
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.702	Intermediate Similarity	NPD6584	Phase 3
0.7019	Intermediate Similarity	NPD7124	Phase 2
0.7018	Intermediate Similarity	NPD6071	Discontinued
0.7011	Intermediate Similarity	NPD8156	Discontinued
0.7007	Intermediate Similarity	NPD4059	Approved
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5960	Phase 3
0.6989	Remote Similarity	NPD6559	Discontinued
0.6988	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4097	Suspended
0.6982	Remote Similarity	NPD4055	Discovery
0.6981	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2424	Discontinued
0.6975	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4357	Discontinued
0.6966	Remote Similarity	NPD7340	Approved
0.6962	Remote Similarity	NPD2161	Phase 2
0.6954	Remote Similarity	NPD8099	Discontinued
0.6954	Remote Similarity	NPD3751	Discontinued
0.6954	Remote Similarity	NPD8251	Approved
0.6954	Remote Similarity	NPD8252	Approved
0.695	Remote Similarity	NPD4750	Phase 3

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