NPASS Compound

Structure

CID43490 OpenBabel06191715372D 29 33 0 0 1 0 0 0 0 0999 V2000 -2.9408 -0.2511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5102 -0.8407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1520 -1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6318 -1.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2149 -0.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8294 -0.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7823 1.2726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2526 0.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6478 0.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5553 -0.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7823 0.7177 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6478 0.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5493 0.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 1.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5493 0.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5114 -0.1167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5493 0.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6619 0.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1324 -0.7910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4548 -0.1502 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5493 0.3171 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3254 -0.0741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 2.0509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3135 0.3971 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 -1.0090 -0.7910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 22 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 12 7 1 1 0 0 0 12 20 1 0 0 0 0 13 24 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 1 0 0 0 18 19 1 0 0 0 0 19 26 2 0 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 21 29 1 0 0 0 0 22 23 1 1 0 0 0 22 29 1 0 0 0 0 23 14 1 1 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	397.868
LogP:	3.921
LogD:	2.948
LogS:	-4.347
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.744
Synthetic Accessibility Score:	6.263
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82
MDCK Permeability:	1.59708706632955e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.261
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.359
Plasma Protein Binding (PPB):	87.11974334716797%
Volume Distribution (VD):	1.758
Pgp-substrate:	9.93065357208252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.698
CYP1A2-substrate:	0.276
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.348
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.375
CYP2D6-inhibitor:	0.779
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	14.65
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.264
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.443
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.437
Carcinogencity:	0.43
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC43490

Natural Product ID:	NPC43490
*Common Name:**	Cochinchinoxanthone
IUPAC Name:	n.a.
Synonyms:	Cochinchinoxanthone
Standard InCHIKey:	XCRBRZWMQVMPIY-OJVGWFQVSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-11(2)5-6-22-20(27)12-7-14-19(26)18-15(25)9-13(24)10-16(18)28-23(14,22)17(8-12)21(3,4)29-22/h5,7,9-10,12,17,24-25H,6,8H2,1-4H3/t12-,17+,22+,23-/m0/s1
SMILES:	CC(=CC[C@@]12OC([C@@H]3[C@@]42Oc2cc(O)cc(c2C(=O)C4=C[C@H](C1=O)C3)O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782238
PubChem CID:	53355017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15182859]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[16310231]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[16651783]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428375]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24928	Cratoxylum cochinchinense	Species	Hypericaceae	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
ED50	1
IC50	3

Activity Type	# Activity
Cell Line	2
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.8	uM	PMID[545219]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	3300.0	nM	PMID[545219]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	6600.0	nM	PMID[545220]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	10000.0	nM	PMID[545219]

☑ 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 NPC43490 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	444
0.1-0.2	1655
0.2-0.3	3277
0.3-0.4	7807
0.4-0.5	10349
0.5-0.6	5225
0.6-0.7	5977
0.7-0.8	6975
0.8-0.85	888
0.85-0.9	50
0.9-0.95	29
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475107
0.9869	High Similarity	NPC94796
0.9679	High Similarity	NPC476255
0.9679	High Similarity	NPC62444
0.9679	High Similarity	NPC476056
0.9677	High Similarity	NPC476931
0.9618	High Similarity	NPC193222
0.961	High Similarity	NPC286422
0.9427	High Similarity	NPC131578
0.9379	High Similarity	NPC475080
0.9367	High Similarity	NPC189689
0.9299	High Similarity	NPC476929
0.925	High Similarity	NPC223413
0.9231	High Similarity	NPC476930
0.9193	High Similarity	NPC55422
0.9193	High Similarity	NPC75141
0.9193	High Similarity	NPC476216
0.9193	High Similarity	NPC47634
0.908	High Similarity	NPC118128
0.908	High Similarity	NPC169018
0.908	High Similarity	NPC476159
0.9074	High Similarity	NPC40089
0.9074	High Similarity	NPC41598
0.9074	High Similarity	NPC476146
0.9074	High Similarity	NPC158329
0.9068	High Similarity	NPC475109
0.9032	High Similarity	NPC476162
0.9024	High Similarity	NPC476229
0.9024	High Similarity	NPC476139
0.9	High Similarity	NPC475106
0.8987	High Similarity	NPC201127
0.8957	High Similarity	NPC63514
0.8931	High Similarity	NPC125969
0.8916	High Similarity	NPC98943
0.8909	High Similarity	NPC476152
0.8902	High Similarity	NPC476196
0.8862	High Similarity	NPC233978
0.8855	High Similarity	NPC162248
0.8831	High Similarity	NPC473135
0.8831	High Similarity	NPC470676
0.8831	High Similarity	NPC473132
0.8805	High Similarity	NPC164427
0.8795	High Similarity	NPC476311
0.8758	High Similarity	NPC204469
0.875	High Similarity	NPC474637
0.875	High Similarity	NPC5671
0.8734	High Similarity	NPC288534
0.871	High Similarity	NPC329678
0.8704	High Similarity	NPC61382
0.8704	High Similarity	NPC103816
0.8698	High Similarity	NPC473607
0.8698	High Similarity	NPC476273
0.8696	High Similarity	NPC264932
0.8696	High Similarity	NPC311574
0.8683	High Similarity	NPC469393
0.8675	High Similarity	NPC315306
0.8675	High Similarity	NPC313717
0.8671	High Similarity	NPC305965
0.8671	High Similarity	NPC471229
0.8662	High Similarity	NPC473978
0.8659	High Similarity	NPC316262
0.8659	High Similarity	NPC314653
0.8645	High Similarity	NPC470673
0.8645	High Similarity	NPC117716
0.8645	High Similarity	NPC470674
0.8642	High Similarity	NPC313368
0.8642	High Similarity	NPC172687
0.8639	High Similarity	NPC476199
0.8639	High Similarity	NPC476210
0.8639	High Similarity	NPC221820
0.8634	High Similarity	NPC161650
0.8634	High Similarity	NPC210048
0.8631	High Similarity	NPC475398
0.8631	High Similarity	NPC245975
0.8627	High Similarity	NPC477272
0.8625	High Similarity	NPC234485
0.8625	High Similarity	NPC476169
0.8623	High Similarity	NPC477529
0.8618	High Similarity	NPC474487
0.8618	High Similarity	NPC474504
0.8618	High Similarity	NPC470672
0.8618	High Similarity	NPC470671
0.8616	High Similarity	NPC470353
0.8616	High Similarity	NPC210597
0.8616	High Similarity	NPC275878
0.8614	High Similarity	NPC54903
0.8614	High Similarity	NPC286074
0.8608	High Similarity	NPC267117
0.8608	High Similarity	NPC150928
0.8606	High Similarity	NPC17274
0.8606	High Similarity	NPC85047
0.8606	High Similarity	NPC120857
0.8598	High Similarity	NPC159508
0.8598	High Similarity	NPC472581
0.859	High Similarity	NPC477955
0.8588	High Similarity	NPC473729
0.858	High Similarity	NPC227275
0.8571	High Similarity	NPC470352
0.8571	High Similarity	NPC470354
0.8571	High Similarity	NPC73899
0.8571	High Similarity	NPC17105
0.8571	High Similarity	NPC147363
0.8571	High Similarity	NPC472050
0.8571	High Similarity	NPC474276
0.8562	High Similarity	NPC236756
0.8562	High Similarity	NPC203080
0.8562	High Similarity	NPC209760
0.8562	High Similarity	NPC311579
0.8562	High Similarity	NPC127172
0.8562	High Similarity	NPC214632
0.8562	High Similarity	NPC100134
0.8562	High Similarity	NPC189130
0.8554	High Similarity	NPC150131
0.8554	High Similarity	NPC478060
0.8554	High Similarity	NPC292233
0.8554	High Similarity	NPC471975
0.8554	High Similarity	NPC470377
0.8554	High Similarity	NPC470374
0.8554	High Similarity	NPC478059
0.8554	High Similarity	NPC126204
0.8553	High Similarity	NPC472580
0.8553	High Similarity	NPC81474
0.8553	High Similarity	NPC46882
0.8553	High Similarity	NPC132990
0.8547	High Similarity	NPC476170
0.8544	High Similarity	NPC65775
0.8544	High Similarity	NPC10027
0.8544	High Similarity	NPC277032
0.8537	High Similarity	NPC219861
0.8529	High Similarity	NPC77179
0.8529	High Similarity	NPC23553
0.8528	High Similarity	NPC243701
0.8528	High Similarity	NPC470810
0.8528	High Similarity	NPC471973
0.8519	High Similarity	NPC474681
0.8519	High Similarity	NPC136674
0.8519	High Similarity	NPC218313
0.8516	High Similarity	NPC144499
0.8512	High Similarity	NPC91650
0.8509	High Similarity	NPC175192
0.8509	High Similarity	NPC255807
0.8509	High Similarity	NPC31018
0.8509	High Similarity	NPC326910
0.8509	High Similarity	NPC471456
0.8509	High Similarity	NPC471116
0.8506	High Similarity	NPC469818
0.8503	High Similarity	NPC20734
0.8503	High Similarity	NPC152477
0.85	High Similarity	NPC142527
0.85	High Similarity	NPC473996
0.85	High Similarity	NPC470340
0.85	High Similarity	NPC477957
0.8494	Intermediate Similarity	NPC477517
0.8494	Intermediate Similarity	NPC235610
0.8494	Intermediate Similarity	NPC469394
0.8491	Intermediate Similarity	NPC475717
0.8491	Intermediate Similarity	NPC471115
0.8491	Intermediate Similarity	NPC29777
0.8488	Intermediate Similarity	NPC8927
0.8488	Intermediate Similarity	NPC246153
0.8485	Intermediate Similarity	NPC109180
0.8485	Intermediate Similarity	NPC273959
0.8485	Intermediate Similarity	NPC469395
0.8481	Intermediate Similarity	NPC39195
0.8481	Intermediate Similarity	NPC296869
0.848	Intermediate Similarity	NPC244903
0.8476	Intermediate Similarity	NPC472906
0.8476	Intermediate Similarity	NPC234644
0.8476	Intermediate Similarity	NPC117985
0.8476	Intermediate Similarity	NPC478134
0.8471	Intermediate Similarity	NPC299011
0.8471	Intermediate Similarity	NPC82534
0.8471	Intermediate Similarity	NPC196114
0.8466	Intermediate Similarity	NPC55738
0.8466	Intermediate Similarity	NPC204879
0.8466	Intermediate Similarity	NPC477410
0.8462	Intermediate Similarity	NPC38219
0.8462	Intermediate Similarity	NPC106985
0.8462	Intermediate Similarity	NPC473813
0.8462	Intermediate Similarity	NPC473812
0.8462	Intermediate Similarity	NPC166138
0.8462	Intermediate Similarity	NPC18585
0.8462	Intermediate Similarity	NPC219915
0.8462	Intermediate Similarity	NPC154986
0.8457	Intermediate Similarity	NPC133970
0.8457	Intermediate Similarity	NPC146636
0.8457	Intermediate Similarity	NPC470600
0.8457	Intermediate Similarity	NPC5322
0.8457	Intermediate Similarity	NPC6633
0.8457	Intermediate Similarity	NPC472907
0.8452	Intermediate Similarity	NPC40118
0.8452	Intermediate Similarity	NPC28042
0.8452	Intermediate Similarity	NPC232021
0.8452	Intermediate Similarity	NPC193698
0.8452	Intermediate Similarity	NPC101107
0.8452	Intermediate Similarity	NPC126534
0.8452	Intermediate Similarity	NPC171870
0.8447	Intermediate Similarity	NPC70433
0.8447	Intermediate Similarity	NPC280530
0.8447	Intermediate Similarity	NPC227337

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 NPC43490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	927
0.2-0.3	1749
0.3-0.4	2688
0.4-0.5	1973
0.5-0.6	947
0.6-0.7	332
0.7-0.8	145
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8457	Intermediate Similarity	NPD3882	Suspended
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8291	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD3749	Approved
0.8176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7411	Suspended
0.8049	Intermediate Similarity	NPD1934	Approved
0.8037	Intermediate Similarity	NPD4380	Phase 2
0.8037	Intermediate Similarity	NPD6599	Discontinued
0.8025	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD1512	Approved
0.8	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD2403	Approved
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2532	Approved
0.795	Intermediate Similarity	NPD2534	Approved
0.795	Intermediate Similarity	NPD2533	Approved
0.7939	Intermediate Similarity	NPD6801	Discontinued
0.7929	Intermediate Similarity	NPD1247	Approved
0.7929	Intermediate Similarity	NPD6959	Discontinued
0.7925	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD3750	Approved
0.7911	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6100	Approved
0.7898	Intermediate Similarity	NPD6099	Approved
0.7895	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1511	Approved
0.7861	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7473	Discontinued
0.7844	Intermediate Similarity	NPD3817	Phase 2
0.7834	Intermediate Similarity	NPD1510	Phase 2
0.7821	Intermediate Similarity	NPD1607	Approved
0.7806	Intermediate Similarity	NPD1240	Approved
0.7803	Intermediate Similarity	NPD3818	Discontinued
0.7798	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD6797	Phase 2
0.7736	Intermediate Similarity	NPD1471	Phase 3
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.7727	Intermediate Similarity	NPD7251	Discontinued
0.7709	Intermediate Similarity	NPD8434	Phase 2
0.7706	Intermediate Similarity	NPD919	Approved
0.7706	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7808	Phase 3
0.7684	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.7657	Intermediate Similarity	NPD5844	Phase 1
0.7651	Intermediate Similarity	NPD3226	Approved
0.764	Intermediate Similarity	NPD1243	Approved
0.7636	Intermediate Similarity	NPD5403	Approved
0.7633	Intermediate Similarity	NPD5402	Approved
0.7627	Intermediate Similarity	NPD6559	Discontinued
0.7625	Intermediate Similarity	NPD2344	Approved
0.7614	Intermediate Similarity	NPD7074	Phase 3
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3751	Discontinued
0.7595	Intermediate Similarity	NPD6651	Approved
0.7588	Intermediate Similarity	NPD7768	Phase 2
0.7571	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7054	Approved
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5711	Approved
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4749	Approved
0.7439	Intermediate Similarity	NPD2309	Approved
0.7425	Intermediate Similarity	NPD920	Approved
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.7407	Intermediate Similarity	NPD2346	Discontinued
0.7391	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3787	Discontinued
0.7358	Intermediate Similarity	NPD943	Approved
0.7354	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7390	Discontinued
0.7346	Intermediate Similarity	NPD1551	Phase 2
0.733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4287	Approved
0.7239	Intermediate Similarity	NPD2935	Discontinued
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4908	Phase 1
0.7209	Intermediate Similarity	NPD37	Approved
0.7205	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD6234	Discontinued
0.7186	Intermediate Similarity	NPD3300	Phase 2
0.7184	Intermediate Similarity	NPD4966	Approved
0.7184	Intermediate Similarity	NPD4967	Phase 2
0.7184	Intermediate Similarity	NPD4965	Approved
0.7182	Intermediate Similarity	NPD5953	Discontinued
0.7173	Intermediate Similarity	NPD6782	Approved
0.7173	Intermediate Similarity	NPD6776	Approved
0.7173	Intermediate Similarity	NPD6779	Approved
0.7173	Intermediate Similarity	NPD6778	Approved
0.7173	Intermediate Similarity	NPD6781	Approved
0.7173	Intermediate Similarity	NPD6780	Approved
0.7173	Intermediate Similarity	NPD6777	Approved
0.717	Intermediate Similarity	NPD4625	Phase 3
0.7168	Intermediate Similarity	NPD5761	Phase 2
0.7168	Intermediate Similarity	NPD5760	Phase 2
0.7158	Intermediate Similarity	NPD8313	Approved
0.7158	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7125	Intermediate Similarity	NPD3764	Approved
0.7125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2313	Discontinued
0.7119	Intermediate Similarity	NPD7199	Phase 2
0.7111	Intermediate Similarity	NPD7228	Approved
0.7108	Intermediate Similarity	NPD2654	Approved
0.7105	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7094	Intermediate Similarity	NPD7907	Approved
0.7089	Intermediate Similarity	NPD2798	Approved
0.7079	Intermediate Similarity	NPD4111	Phase 1
0.7079	Intermediate Similarity	NPD4665	Approved
0.7072	Intermediate Similarity	NPD7286	Phase 2
0.7062	Intermediate Similarity	NPD7697	Approved
0.7062	Intermediate Similarity	NPD7696	Phase 3
0.7062	Intermediate Similarity	NPD7698	Approved
0.7051	Intermediate Similarity	NPD9717	Approved
0.7049	Intermediate Similarity	NPD6764	Approved
0.7049	Intermediate Similarity	NPD6765	Approved
0.7044	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7458	Discontinued
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4288	Approved
0.7026	Intermediate Similarity	NPD7871	Phase 2
0.7026	Intermediate Similarity	NPD7870	Phase 2
0.7025	Intermediate Similarity	NPD1203	Approved
0.7025	Intermediate Similarity	NPD1470	Approved
0.701	Intermediate Similarity	NPD3057	Approved
0.7	Intermediate Similarity	NPD4363	Phase 3
0.7	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4360	Phase 2
0.6994	Remote Similarity	NPD5124	Phase 1
0.6994	Remote Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1610	Phase 2
0.6983	Remote Similarity	NPD7229	Phase 3
0.697	Remote Similarity	NPD8151	Discontinued
0.697	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4308	Phase 3
0.6963	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4361	Phase 2
0.6941	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7874	Approved
0.6935	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4060	Phase 1
0.6932	Remote Similarity	NPD2296	Approved
0.6928	Remote Similarity	NPD5408	Approved
0.6928	Remote Similarity	NPD5405	Approved
0.6928	Remote Similarity	NPD5404	Approved
0.6928	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD3533	Approved
0.6923	Remote Similarity	NPD2972	Approved
0.6923	Remote Similarity	NPD2354	Approved
0.6923	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7701	Phase 2
0.6918	Remote Similarity	NPD2797	Approved
0.6918	Remote Similarity	NPD3266	Approved
0.6918	Remote Similarity	NPD3267	Approved
0.6914	Remote Similarity	NPD411	Approved
0.6911	Remote Similarity	NPD6534	Approved
0.6911	Remote Similarity	NPD6535	Approved
0.69	Remote Similarity	NPD7801	Approved
0.6898	Remote Similarity	NPD6784	Approved
0.6898	Remote Similarity	NPD6785	Approved
0.6897	Remote Similarity	NPD7028	Phase 2
0.689	Remote Similarity	NPD1933	Approved
0.6879	Remote Similarity	NPD1201	Approved
0.6879	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD422	Phase 1
0.6872	Remote Similarity	NPD2494	Approved
0.6872	Remote Similarity	NPD2493	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