NPASS Compound

Structure

NPC19238 OpenBabel07101718272D 30 33 0 0 1 0 0 0 0 0999 V2000 -0.0000 6.0000 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 -3.4641 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 3.4641 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 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 -0.0000 3.0000 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 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 -0.8660 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 2.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1.7321 3.0000 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 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 4 1 1 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 19 26 2 0 0 0 0 19 30 1 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 27 2 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.16
Volume:	424.317
LogP:	5.988
LogD:	3.75
LogS:	-5.218
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.475
Synthetic Accessibility Score:	3.647
Fsp3:	0.28
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:	-4.8
MDCK Permeability:	1.6425981812062673e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	91.09493255615234%
Volume Distribution (VD):	0.493
Pgp-substrate:	6.26524019241333%

ADMET: Metabolism

CYP1A2-inhibitor:	0.521
CYP1A2-substrate:	0.404
CYP2C19-inhibitor:	0.865
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.097
CYP2D6-substrate:	0.292
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	6.338
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.806
Maximum Recommended Daily Dose:	0.189
Skin Sensitization:	0.263
Carcinogencity:	0.221
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.234

Download Data

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

Natural Product: NPC19238

Natural Product ID:	NPC19238
*Common Name:**	Brasimarin C
IUPAC Name:	(8R,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-enyl)-4-phenyl-8,9-dihydropyrano[2,3-f]chromene-2,10-dione
Synonyms:	Brasimarin C
Standard InCHIKey:	ZJXOEBUGDGYYOO-HUUCEWRRSA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-13(2)10-11-17-23(28)20-18(16-8-6-5-7-9-16)12-19(26)30-25(20)21-22(27)14(3)15(4)29-24(17)21/h5-10,12,14-15,28H,11H2,1-4H3/t14-,15-/m1/s1
SMILES:	CC(=CCc1c(O)c2c(cc(=O)oc2c2c1O[C@H](C)[C@H](C2=O)C)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476875
PubChem CID:	10341168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908963]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662094]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104480]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15340243]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	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
Others	8

Activity Type	# Activity
Cell Line	6
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[464885]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[464885]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4400.0	nM	PMID[464886]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	10100.0	nM	PMID[464886]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[464885]
NPT2	Others	Unspecified		Activity	=	33.3	%	PMID[464885]
NPT2	Others	Unspecified		Activity	=	70.2	%	PMID[464885]
NPT2	Others	Unspecified		Activity	=	93.8	%	PMID[464885]
NPT2	Others	Unspecified		IC50	=	348.0	molar ratio	PMID[464885]

☑ 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 NPC19238 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	361
0.1-0.2	1532
0.2-0.3	3470
0.3-0.4	8284
0.4-0.5	10535
0.5-0.6	3885
0.6-0.7	5874
0.7-0.8	4725
0.8-0.85	2400
0.85-0.9	1318
0.9-0.95	267
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.986	High Similarity	NPC164205
0.986	High Similarity	NPC104236
0.9724	High Similarity	NPC209142
0.9724	High Similarity	NPC312549
0.9655	High Similarity	NPC474735
0.965	High Similarity	NPC470322
0.9648	High Similarity	NPC188632
0.9648	High Similarity	NPC112791
0.9648	High Similarity	NPC94794
0.9648	High Similarity	NPC87609
0.9648	High Similarity	NPC470296
0.9648	High Similarity	NPC196459
0.9589	High Similarity	NPC290671
0.9583	High Similarity	NPC249942
0.9583	High Similarity	NPC297886
0.9583	High Similarity	NPC140120
0.958	High Similarity	NPC469935
0.958	High Similarity	NPC1886
0.958	High Similarity	NPC178627
0.958	High Similarity	NPC196137
0.9577	High Similarity	NPC36181
0.9517	High Similarity	NPC161864
0.9517	High Similarity	NPC469933
0.9517	High Similarity	NPC208303
0.9514	High Similarity	NPC267375
0.9514	High Similarity	NPC88964
0.9514	High Similarity	NPC312973
0.9514	High Similarity	NPC20488
0.9514	High Similarity	NPC475052
0.9514	High Similarity	NPC476088
0.9514	High Similarity	NPC67805
0.9514	High Similarity	NPC246948
0.9514	High Similarity	NPC111786
0.9514	High Similarity	NPC57470
0.9514	High Similarity	NPC474161
0.9514	High Similarity	NPC470647
0.9514	High Similarity	NPC181388
0.9514	High Similarity	NPC54577
0.9514	High Similarity	NPC154217
0.9514	High Similarity	NPC83357
0.9514	High Similarity	NPC176229
0.9514	High Similarity	NPC142405
0.9514	High Similarity	NPC214774
0.9514	High Similarity	NPC301276
0.9514	High Similarity	NPC195621
0.951	High Similarity	NPC125894
0.951	High Similarity	NPC278249
0.951	High Similarity	NPC81697
0.951	High Similarity	NPC77794
0.951	High Similarity	NPC85162
0.951	High Similarity	NPC107177
0.951	High Similarity	NPC223812
0.9507	High Similarity	NPC110038
0.9507	High Similarity	NPC248372
0.9456	High Similarity	NPC309512
0.9456	High Similarity	NPC148945
0.9456	High Similarity	NPC204561
0.9456	High Similarity	NPC78835
0.9456	High Similarity	NPC317715
0.9456	High Similarity	NPC316960
0.9452	High Similarity	NPC469932
0.9448	High Similarity	NPC23728
0.9448	High Similarity	NPC283234
0.9448	High Similarity	NPC282335
0.9448	High Similarity	NPC296998
0.9448	High Similarity	NPC473077
0.9448	High Similarity	NPC218300
0.9448	High Similarity	NPC110303
0.9448	High Similarity	NPC180477
0.9444	High Similarity	NPC473014
0.9444	High Similarity	NPC319752
0.9444	High Similarity	NPC235217
0.9444	High Similarity	NPC131568
0.9444	High Similarity	NPC473013
0.9444	High Similarity	NPC469953
0.9444	High Similarity	NPC131579
0.9444	High Similarity	NPC473015
0.9441	High Similarity	NPC66515
0.9441	High Similarity	NPC296917
0.9441	High Similarity	NPC32739
0.9441	High Similarity	NPC76372
0.9441	High Similarity	NPC107572
0.9441	High Similarity	NPC324134
0.9441	High Similarity	NPC166934
0.9441	High Similarity	NPC324436
0.9441	High Similarity	NPC194432
0.9441	High Similarity	NPC161506
0.9441	High Similarity	NPC37496
0.9441	High Similarity	NPC228504
0.9441	High Similarity	NPC167624
0.9441	High Similarity	NPC227579
0.9441	High Similarity	NPC220998
0.9441	High Similarity	NPC78
0.9441	High Similarity	NPC166482
0.9441	High Similarity	NPC223500
0.9441	High Similarity	NPC76338
0.9441	High Similarity	NPC10937
0.9441	High Similarity	NPC265040
0.9441	High Similarity	NPC177354
0.9441	High Similarity	NPC40833
0.9441	High Similarity	NPC64915
0.9441	High Similarity	NPC182852
0.9441	High Similarity	NPC328164
0.9441	High Similarity	NPC306829
0.9441	High Similarity	NPC1089
0.9441	High Similarity	NPC125855
0.9441	High Similarity	NPC148757
0.9384	High Similarity	NPC160821
0.9384	High Similarity	NPC132592
0.9384	High Similarity	NPC161191
0.9379	High Similarity	NPC127059
0.9379	High Similarity	NPC470131
0.9379	High Similarity	NPC470134
0.9379	High Similarity	NPC473078
0.9379	High Similarity	NPC109183
0.9379	High Similarity	NPC470133
0.9379	High Similarity	NPC285630
0.9379	High Similarity	NPC228779
0.9379	High Similarity	NPC470132
0.9375	High Similarity	NPC149026
0.9375	High Similarity	NPC478086
0.9375	High Similarity	NPC257097
0.9375	High Similarity	NPC150408
0.9375	High Similarity	NPC68104
0.9375	High Similarity	NPC185276
0.9375	High Similarity	NPC310130
0.9375	High Similarity	NPC214166
0.9375	High Similarity	NPC91560
0.9375	High Similarity	NPC75049
0.9375	High Similarity	NPC143896
0.9375	High Similarity	NPC164980
0.9375	High Similarity	NPC316816
0.9375	High Similarity	NPC169591
0.9375	High Similarity	NPC175504
0.9375	High Similarity	NPC221432
0.9375	High Similarity	NPC39329
0.9371	High Similarity	NPC96408
0.9371	High Similarity	NPC4743
0.9371	High Similarity	NPC213322
0.9371	High Similarity	NPC258630
0.9371	High Similarity	NPC17170
0.9371	High Similarity	NPC156190
0.9371	High Similarity	NPC279650
0.9371	High Similarity	NPC312391
0.9371	High Similarity	NPC166689
0.9371	High Similarity	NPC282300
0.9371	High Similarity	NPC324386
0.9366	High Similarity	NPC217186
0.9366	High Similarity	NPC53181
0.9333	High Similarity	NPC321372
0.9333	High Similarity	NPC78554
0.9333	High Similarity	NPC474738
0.9333	High Similarity	NPC474609
0.9333	High Similarity	NPC109967
0.9333	High Similarity	NPC129053
0.9333	High Similarity	NPC469936
0.9333	High Similarity	NPC475797
0.932	High Similarity	NPC473016
0.9315	High Similarity	NPC474108
0.9315	High Similarity	NPC177995
0.931	High Similarity	NPC39045
0.931	High Similarity	NPC209040
0.931	High Similarity	NPC271288
0.931	High Similarity	NPC236766
0.931	High Similarity	NPC470136
0.931	High Similarity	NPC470135
0.931	High Similarity	NPC197252
0.9306	High Similarity	NPC470556
0.9306	High Similarity	NPC266725
0.9301	High Similarity	NPC159275
0.9301	High Similarity	NPC110228
0.9301	High Similarity	NPC76445
0.9301	High Similarity	NPC241100
0.9301	High Similarity	NPC284550
0.9301	High Similarity	NPC6407
0.9301	High Similarity	NPC129853
0.9301	High Similarity	NPC188243
0.9267	High Similarity	NPC108937
0.9267	High Similarity	NPC279218
0.9257	High Similarity	NPC29777
0.9257	High Similarity	NPC471115
0.9257	High Similarity	NPC472633
0.9257	High Similarity	NPC151973
0.9252	High Similarity	NPC189087
0.9252	High Similarity	NPC321623
0.9247	High Similarity	NPC472629
0.9247	High Similarity	NPC2416
0.9247	High Similarity	NPC215885
0.9247	High Similarity	NPC476153
0.9241	High Similarity	NPC470553
0.9241	High Similarity	NPC96216
0.9241	High Similarity	NPC474939
0.9241	High Similarity	NPC471621
0.9241	High Similarity	NPC38219
0.9241	High Similarity	NPC219915
0.9241	High Similarity	NPC470909
0.9241	High Similarity	NPC307895
0.9236	High Similarity	NPC470555
0.9236	High Similarity	NPC110969
0.9236	High Similarity	NPC201820

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 NPC19238 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	945
0.2-0.3	1551
0.3-0.4	2519
0.4-0.5	2039
0.5-0.6	1172
0.6-0.7	403
0.7-0.8	129
0.8-0.85	40
0.85-0.9	23
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9195	High Similarity	NPD7411	Suspended
0.9091	High Similarity	NPD1552	Clinical (unspecified phase)
0.9091	High Similarity	NPD1550	Clinical (unspecified phase)
0.9048	High Similarity	NPD7410	Clinical (unspecified phase)
0.9048	High Similarity	NPD4378	Clinical (unspecified phase)
0.9028	High Similarity	NPD1549	Phase 2
0.902	High Similarity	NPD7075	Discontinued
0.9013	High Similarity	NPD8443	Clinical (unspecified phase)
0.8947	High Similarity	NPD7096	Clinical (unspecified phase)
0.8882	High Similarity	NPD6801	Discontinued
0.8874	High Similarity	NPD4380	Phase 2
0.8824	High Similarity	NPD7819	Suspended
0.8824	High Similarity	NPD2393	Clinical (unspecified phase)
0.8759	High Similarity	NPD2796	Approved
0.869	High Similarity	NPD1510	Phase 2
0.8679	High Similarity	NPD7852	Clinical (unspecified phase)
0.8654	High Similarity	NPD4381	Clinical (unspecified phase)
0.86	High Similarity	NPD6799	Approved
0.859	High Similarity	NPD7768	Phase 2
0.8581	High Similarity	NPD7421	Clinical (unspecified phase)
0.8542	High Similarity	NPD1240	Approved
0.8523	High Similarity	NPD3750	Approved
0.8519	High Similarity	NPD7804	Clinical (unspecified phase)
0.8516	High Similarity	NPD1934	Approved
0.8483	Intermediate Similarity	NPD5124	Phase 1
0.8483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD5403	Approved
0.8425	Intermediate Similarity	NPD1607	Approved
0.8418	Intermediate Similarity	NPD3749	Approved
0.8403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6599	Discontinued
0.8375	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD1243	Approved
0.8312	Intermediate Similarity	NPD920	Approved
0.8301	Intermediate Similarity	NPD5401	Approved
0.8291	Intermediate Similarity	NPD3817	Phase 2
0.8289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1551	Phase 2
0.8239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1511	Approved
0.8228	Intermediate Similarity	NPD2801	Approved
0.8221	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5494	Approved
0.8188	Intermediate Similarity	NPD3748	Approved
0.8188	Intermediate Similarity	NPD2799	Discontinued
0.8182	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8182	Intermediate Similarity	NPD2533	Approved
0.8176	Intermediate Similarity	NPD6651	Approved
0.8151	Intermediate Similarity	NPD2313	Discontinued
0.8151	Intermediate Similarity	NPD3268	Approved
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7472	Approved
0.8129	Intermediate Similarity	NPD1512	Approved
0.8095	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2800	Approved
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8084	Intermediate Similarity	NPD5953	Discontinued
0.8072	Intermediate Similarity	NPD7286	Phase 2
0.8067	Intermediate Similarity	NPD7033	Discontinued
0.8063	Intermediate Similarity	NPD5402	Approved
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD2797	Approved
0.8056	Intermediate Similarity	NPD1203	Approved
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6559	Discontinued
0.8036	Intermediate Similarity	NPD7251	Discontinued
0.8027	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6832	Phase 2
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7808	Phase 3
0.7987	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4628	Phase 3
0.7914	Intermediate Similarity	NPD919	Approved
0.7902	Intermediate Similarity	NPD422	Phase 1
0.7891	Intermediate Similarity	NPD4908	Phase 1
0.7862	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD3225	Approved
0.7853	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD9717	Approved
0.7843	Intermediate Similarity	NPD2346	Discontinued
0.7841	Intermediate Similarity	NPD4360	Phase 2
0.7841	Intermediate Similarity	NPD4363	Phase 3
0.7834	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3267	Approved
0.7808	Intermediate Similarity	NPD3266	Approved
0.7806	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5889	Approved
0.7764	Intermediate Similarity	NPD5890	Approved
0.775	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4308	Phase 3
0.7669	Intermediate Similarity	NPD1465	Phase 2
0.7665	Intermediate Similarity	NPD5711	Approved
0.7665	Intermediate Similarity	NPD5710	Approved
0.7662	Intermediate Similarity	NPD6100	Approved
0.7662	Intermediate Similarity	NPD6099	Approved
0.7655	Intermediate Similarity	NPD1610	Phase 2
0.764	Intermediate Similarity	NPD7458	Discontinued
0.7635	Intermediate Similarity	NPD2798	Approved
0.7622	Intermediate Similarity	NPD1548	Phase 1
0.7613	Intermediate Similarity	NPD2344	Approved
0.7593	Intermediate Similarity	NPD6585	Discontinued
0.755	Intermediate Similarity	NPD6798	Discontinued
0.755	Intermediate Similarity	NPD1296	Phase 2
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7528	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1652	Phase 2
0.7515	Intermediate Similarity	NPD4288	Approved
0.7514	Intermediate Similarity	NPD4287	Approved
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1608	Approved
0.7471	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.7453	Intermediate Similarity	NPD6273	Approved
0.7451	Intermediate Similarity	NPD4307	Phase 2
0.7438	Intermediate Similarity	NPD7390	Discontinued
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7421	Intermediate Similarity	NPD2309	Approved
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6355	Discontinued
0.74	Intermediate Similarity	NPD1019	Discontinued
0.7396	Intermediate Similarity	NPD1247	Approved
0.7389	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6004	Phase 3
0.7389	Intermediate Similarity	NPD6002	Phase 3
0.7389	Intermediate Similarity	NPD6005	Phase 3
0.7389	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7584	Approved
0.7361	Intermediate Similarity	NPD9493	Approved
0.7349	Intermediate Similarity	NPD8455	Phase 2
0.7338	Intermediate Similarity	NPD943	Approved
0.732	Intermediate Similarity	NPD411	Approved
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1729	Discontinued
0.7296	Intermediate Similarity	NPD2654	Approved
0.7294	Intermediate Similarity	NPD7199	Phase 2
0.729	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD230	Phase 1
0.7283	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.726	Intermediate Similarity	NPD1894	Discontinued
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7249	Intermediate Similarity	NPD7585	Approved
0.7239	Intermediate Similarity	NPD5049	Phase 3
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7219	Intermediate Similarity	NPD1164	Approved
0.7215	Intermediate Similarity	NPD4477	Approved
0.7215	Intermediate Similarity	NPD4476	Approved
0.7212	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3926	Phase 2
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3764	Approved
0.7207	Intermediate Similarity	NPD8150	Discontinued
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7205	Intermediate Similarity	NPD3887	Approved
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7196	Intermediate Similarity	NPD7583	Approved
0.719	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6844	Discontinued
0.7186	Intermediate Similarity	NPD37	Approved
0.7184	Intermediate Similarity	NPD7177	Discontinued
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD6234	Discontinued
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4965	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD1653	Approved
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD7782	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