NPASS Compound

Structure

NPC278600 OpenBabel07101719252D 30 34 0 0 1 0 0 0 0 0999 V2000 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 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 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 1.7321 -2.0000 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 -1.7321 1.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 -0.0000 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 -3.5000 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 -2.5981 -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 1 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 -0.8660 -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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 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 -3.4641 -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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 25 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 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 25 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 1 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 2 1 1 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 18 26 2 0 0 0 0 18 29 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 27 1 1 0 0 0 22 28 1 0 0 0 0 23 30 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:	418.397
LogP:	5.932
LogD:	4.637
LogS:	-3.892
# Rotatable Bonds:	1
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	3.967
Fsp3:	0.32
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:	-4.735
MDCK Permeability:	1.666076605033595e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	93.24436950683594%
Volume Distribution (VD):	0.746
Pgp-substrate:	5.389237403869629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.467
CYP1A2-substrate:	0.695
CYP2C19-inhibitor:	0.775
CYP2C19-substrate:	0.248
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.515
CYP2D6-substrate:	0.26
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	2.957
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.879
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.608
Skin Sensitization:	0.253
Carcinogencity:	0.739
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC278600

Natural Product ID:	NPC278600
*Common Name:**	BXENDTPSKAICGV-QTCYRWPVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BXENDTPSKAICGV-QTCYRWPVSA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-13-14(2)28-22-16-10-11-25(3,4)30-23(16)19-17(15-8-6-5-7-9-15)12-18(26)29-24(19)20(22)21(13)27/h5-14,21,27H,1-4H3/t13-,14+,21-/m0/s1
SMILES:	C[C@H]1[C@@H](C)Oc2c3C=CC(C)(C)Oc3c3c(cc(=O)oc3c2[C@H]1O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL132692
PubChem CID:	455248
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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	30000.0	nM	PMID[509469]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	33000.0	nM	PMID[509469]

☑ 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 NPC278600 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	359
0.1-0.2	1587
0.2-0.3	3382
0.3-0.4	8343
0.4-0.5	10731
0.5-0.6	4041
0.6-0.7	6138
0.7-0.8	5257
0.8-0.85	1939
0.85-0.9	781
0.9-0.95	121
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37428
1.0	High Similarity	NPC47040
1.0	High Similarity	NPC35501
1.0	High Similarity	NPC137262
1.0	High Similarity	NPC144512
0.9618	High Similarity	NPC469952
0.9618	High Similarity	NPC241165
0.9618	High Similarity	NPC1220
0.9618	High Similarity	NPC205797
0.9618	High Similarity	NPC142563
0.9618	High Similarity	NPC291551
0.9618	High Similarity	NPC469955
0.9618	High Similarity	NPC141822
0.9394	High Similarity	NPC469956
0.9323	High Similarity	NPC469965
0.9254	High Similarity	NPC131950
0.9237	High Similarity	NPC293642
0.9237	High Similarity	NPC139595
0.9237	High Similarity	NPC60704
0.9143	High Similarity	NPC475719
0.9143	High Similarity	NPC101255
0.9143	High Similarity	NPC106126
0.9143	High Similarity	NPC43716
0.9143	High Similarity	NPC108994
0.9124	High Similarity	NPC279573
0.9098	High Similarity	NPC32463
0.9058	High Similarity	NPC71903
0.9037	High Similarity	NPC31849
0.9007	High Similarity	NPC469701
0.8993	High Similarity	NPC195357
0.8993	High Similarity	NPC287286
0.8993	High Similarity	NPC152771
0.8993	High Similarity	NPC170812
0.8986	High Similarity	NPC211110
0.8921	High Similarity	NPC312881
0.8913	High Similarity	NPC225106
0.8913	High Similarity	NPC232246
0.8913	High Similarity	NPC294456
0.8913	High Similarity	NPC212124
0.8913	High Similarity	NPC281014
0.8913	High Similarity	NPC184861
0.8913	High Similarity	NPC153818
0.8897	High Similarity	NPC77196
0.8872	High Similarity	NPC224774
0.8872	High Similarity	NPC149796
0.8872	High Similarity	NPC258567
0.8872	High Similarity	NPC121740
0.8864	High Similarity	NPC232692
0.8864	High Similarity	NPC202594
0.8857	High Similarity	NPC138149
0.8849	High Similarity	NPC151946
0.8841	High Similarity	NPC38099
0.8841	High Similarity	NPC78746
0.8841	High Similarity	NPC188380
0.8841	High Similarity	NPC224543
0.8841	High Similarity	NPC26954
0.8832	High Similarity	NPC50896
0.8832	High Similarity	NPC213173
0.8832	High Similarity	NPC180716
0.8832	High Similarity	NPC224475
0.8832	High Similarity	NPC204353
0.8832	High Similarity	NPC326600
0.8832	High Similarity	NPC62366
0.8824	High Similarity	NPC194277
0.8815	High Similarity	NPC113098
0.8806	High Similarity	NPC185066
0.8806	High Similarity	NPC469453
0.8803	High Similarity	NPC471824
0.8797	High Similarity	NPC276212
0.8794	High Similarity	NPC93640
0.8794	High Similarity	NPC20631
0.8788	High Similarity	NPC291899
0.8777	High Similarity	NPC155963
0.8777	High Similarity	NPC131198
0.8768	High Similarity	NPC86892
0.8768	High Similarity	NPC472525
0.8768	High Similarity	NPC472424
0.8768	High Similarity	NPC471625
0.8768	High Similarity	NPC471909
0.8768	High Similarity	NPC281241
0.8759	High Similarity	NPC167111
0.8759	High Similarity	NPC318400
0.8759	High Similarity	NPC471910
0.8759	High Similarity	NPC133956
0.8759	High Similarity	NPC207002
0.8759	High Similarity	NPC296624
0.875	High Similarity	NPC272650
0.875	High Similarity	NPC250727
0.875	High Similarity	NPC244888
0.875	High Similarity	NPC68205
0.875	High Similarity	NPC118683
0.875	High Similarity	NPC164804
0.875	High Similarity	NPC293203
0.875	High Similarity	NPC267336
0.875	High Similarity	NPC29734
0.875	High Similarity	NPC211413
0.8741	High Similarity	NPC295696
0.8741	High Similarity	NPC226722
0.8741	High Similarity	NPC134360
0.8731	High Similarity	NPC243688
0.8722	High Similarity	NPC168259
0.8722	High Similarity	NPC188022
0.8722	High Similarity	NPC285040
0.8722	High Similarity	NPC17809
0.8722	High Similarity	NPC102540
0.8722	High Similarity	NPC103420
0.8712	High Similarity	NPC315807
0.8712	High Similarity	NPC50720
0.8705	High Similarity	NPC283019
0.8705	High Similarity	NPC160727
0.8705	High Similarity	NPC177281
0.8705	High Similarity	NPC471630
0.8705	High Similarity	NPC149320
0.8705	High Similarity	NPC476455
0.8705	High Similarity	NPC55615
0.8705	High Similarity	NPC128529
0.8699	High Similarity	NPC19238
0.8699	High Similarity	NPC103116
0.8699	High Similarity	NPC164205
0.8699	High Similarity	NPC104236
0.8696	High Similarity	NPC100986
0.8696	High Similarity	NPC296915
0.8696	High Similarity	NPC260265
0.8696	High Similarity	NPC198381
0.8696	High Similarity	NPC164269
0.8696	High Similarity	NPC97834
0.8696	High Similarity	NPC225696
0.8696	High Similarity	NPC127888
0.8696	High Similarity	NPC115335
0.8696	High Similarity	NPC287182
0.8696	High Similarity	NPC166672
0.8696	High Similarity	NPC47163
0.8696	High Similarity	NPC195343
0.8696	High Similarity	NPC184677
0.8696	High Similarity	NPC84894
0.8696	High Similarity	NPC319859
0.8696	High Similarity	NPC267412
0.8696	High Similarity	NPC74655
0.8696	High Similarity	NPC18804
0.8696	High Similarity	NPC198154
0.8696	High Similarity	NPC223008
0.869	High Similarity	NPC282335
0.869	High Similarity	NPC218300
0.8686	High Similarity	NPC19157
0.8667	High Similarity	NPC274717
0.8657	High Similarity	NPC471826
0.8649	High Similarity	NPC223720
0.8647	High Similarity	NPC86502
0.8647	High Similarity	NPC246648
0.8647	High Similarity	NPC106914
0.8647	High Similarity	NPC27671
0.8647	High Similarity	NPC201667
0.8647	High Similarity	NPC197351
0.8647	High Similarity	NPC73413
0.8647	High Similarity	NPC134195
0.8636	High Similarity	NPC150214
0.8623	High Similarity	NPC163557
0.8621	High Similarity	NPC87950
0.8621	High Similarity	NPC471764
0.8613	High Similarity	NPC37009
0.8613	High Similarity	NPC66430
0.8611	High Similarity	NPC85624
0.8603	High Similarity	NPC168710
0.8592	High Similarity	NPC5155
0.8592	High Similarity	NPC310370
0.8592	High Similarity	NPC183642
0.8591	High Similarity	NPC268484
0.8582	High Similarity	NPC244495
0.8582	High Similarity	NPC93219
0.8582	High Similarity	NPC471828
0.8582	High Similarity	NPC471827
0.8571	High Similarity	NPC109675
0.8571	High Similarity	NPC290605
0.8571	High Similarity	NPC273772
0.8571	High Similarity	NPC472518
0.8571	High Similarity	NPC154176
0.8571	High Similarity	NPC143725
0.8571	High Similarity	NPC38761
0.8571	High Similarity	NPC173350
0.8571	High Similarity	NPC76465
0.8562	High Similarity	NPC249942
0.8562	High Similarity	NPC169510
0.8562	High Similarity	NPC297886
0.8562	High Similarity	NPC142863
0.8561	High Similarity	NPC253574
0.8561	High Similarity	NPC98179
0.8551	High Similarity	NPC14248
0.8551	High Similarity	NPC13005
0.8542	High Similarity	NPC36732
0.854	High Similarity	NPC80170
0.8529	High Similarity	NPC38664
0.8529	High Similarity	NPC472519
0.8529	High Similarity	NPC219923
0.8529	High Similarity	NPC53986
0.8514	High Similarity	NPC474735
0.8511	High Similarity	NPC306365
0.8507	High Similarity	NPC111347
0.8503	High Similarity	NPC208303
0.8503	High Similarity	NPC161864
0.8503	High Similarity	NPC161191

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 NPC278600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	953
0.2-0.3	1587
0.3-0.4	2546
0.4-0.5	2092
0.5-0.6	1113
0.6-0.7	361
0.7-0.8	135
0.8-0.85	37
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9618	High Similarity	NPD5124	Phase 1
0.9618	High Similarity	NPD5123	Clinical (unspecified phase)
0.854	High Similarity	NPD4907	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD422	Phase 1
0.8394	Intermediate Similarity	NPD4908	Phase 1
0.8207	Intermediate Similarity	NPD1652	Phase 2
0.8148	Intermediate Similarity	NPD1610	Phase 2
0.8143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD1548	Phase 1
0.8102	Intermediate Similarity	NPD3225	Approved
0.8092	Intermediate Similarity	NPD7411	Suspended
0.8043	Intermediate Similarity	NPD2797	Approved
0.7974	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7033	Discontinued
0.7922	Intermediate Similarity	NPD6801	Discontinued
0.7905	Intermediate Similarity	NPD3750	Approved
0.7887	Intermediate Similarity	NPD3268	Approved
0.7871	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7075	Discontinued
0.7829	Intermediate Similarity	NPD5403	Approved
0.7823	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4625	Phase 3
0.7815	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4380	Phase 2
0.7785	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1613	Approved
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.777	Intermediate Similarity	NPD1549	Phase 2
0.7762	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7819	Suspended
0.7748	Intermediate Similarity	NPD7212	Phase 2
0.7748	Intermediate Similarity	NPD7213	Phase 3
0.774	Intermediate Similarity	NPD7097	Phase 1
0.773	Intermediate Similarity	NPD5844	Phase 1
0.7727	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5401	Approved
0.7687	Intermediate Similarity	NPD3748	Approved
0.7669	Intermediate Similarity	NPD5535	Approved
0.7662	Intermediate Similarity	NPD1653	Approved
0.7655	Intermediate Similarity	NPD4060	Phase 1
0.7654	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4749	Approved
0.7643	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2796	Approved
0.7622	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7447	Phase 1
0.7582	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6667	Approved
0.7566	Intermediate Similarity	NPD6666	Approved
0.7552	Intermediate Similarity	NPD2861	Phase 2
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7549	Discontinued
0.7535	Intermediate Similarity	NPD3266	Approved
0.7535	Intermediate Similarity	NPD3267	Approved
0.7517	Intermediate Similarity	NPD6798	Discontinued
0.7517	Intermediate Similarity	NPD1296	Phase 2
0.7516	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5402	Approved
0.7483	Intermediate Similarity	NPD4340	Discontinued
0.7467	Intermediate Similarity	NPD6004	Phase 3
0.7467	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6002	Phase 3
0.7467	Intermediate Similarity	NPD6005	Phase 3
0.7467	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4308	Phase 3
0.745	Intermediate Similarity	NPD1510	Phase 2
0.7448	Intermediate Similarity	NPD3027	Phase 3
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7431	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8455	Phase 2
0.7417	Intermediate Similarity	NPD2424	Discontinued
0.7415	Intermediate Similarity	NPD4140	Approved
0.74	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD3749	Approved
0.7376	Intermediate Similarity	NPD1091	Approved
0.7368	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6355	Discontinued
0.7362	Intermediate Similarity	NPD6959	Discontinued
0.7358	Intermediate Similarity	NPD1934	Approved
0.7357	Intermediate Similarity	NPD4626	Approved
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6166	Phase 2
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7305	Intermediate Similarity	NPD7054	Approved
0.7305	Intermediate Similarity	NPD3496	Discontinued
0.7303	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1240	Approved
0.7286	Intermediate Similarity	NPD5691	Approved
0.7285	Intermediate Similarity	NPD2935	Discontinued
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD6100	Approved
0.7279	Intermediate Similarity	NPD2313	Discontinued
0.7278	Intermediate Similarity	NPD6559	Discontinued
0.7267	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3817	Phase 2
0.7267	Intermediate Similarity	NPD4538	Approved
0.7267	Intermediate Similarity	NPD4536	Approved
0.7262	Intermediate Similarity	NPD7074	Phase 3
0.7262	Intermediate Similarity	NPD7472	Approved
0.7261	Intermediate Similarity	NPD920	Approved
0.726	Intermediate Similarity	NPD6832	Phase 2
0.7255	Intermediate Similarity	NPD1243	Approved
0.725	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD5762	Approved
0.723	Intermediate Similarity	NPD6233	Phase 2
0.7226	Intermediate Similarity	NPD5058	Phase 3
0.7226	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4967	Phase 2
0.7222	Intermediate Similarity	NPD4965	Approved
0.7222	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD8651	Approved
0.7219	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7218	Intermediate Similarity	NPD3134	Approved
0.7214	Intermediate Similarity	NPD1894	Discontinued
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD7003	Approved
0.7208	Intermediate Similarity	NPD7466	Approved
0.7208	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1607	Approved
0.7197	Intermediate Similarity	NPD6273	Approved
0.7195	Intermediate Similarity	NPD5494	Approved
0.7181	Intermediate Similarity	NPD4307	Phase 2
0.7176	Intermediate Similarity	NPD7251	Discontinued
0.7172	Intermediate Similarity	NPD1203	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD9697	Approved
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7134	Intermediate Similarity	NPD2534	Approved
0.7134	Intermediate Similarity	NPD2533	Approved
0.7134	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2532	Approved
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7111	Intermediate Similarity	NPD2684	Approved
0.7105	Intermediate Similarity	NPD5960	Phase 3
0.7105	Intermediate Similarity	NPD5588	Approved
0.7099	Intermediate Similarity	NPD2801	Approved
0.7095	Intermediate Similarity	NPD7095	Approved
0.7089	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9717	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD1511	Approved
0.7063	Intermediate Similarity	NPD3847	Discontinued
0.7063	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD4476	Approved
0.7041	Intermediate Similarity	NPD3818	Discontinued
0.7037	Intermediate Similarity	NPD290	Approved
0.7037	Intermediate Similarity	NPD4433	Discontinued
0.7037	Intermediate Similarity	NPD1358	Approved
0.7035	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6234	Discontinued
0.7029	Intermediate Similarity	NPD7843	Approved
0.7019	Intermediate Similarity	NPD6502	Phase 2
0.7018	Intermediate Similarity	NPD5953	Discontinued
0.7014	Intermediate Similarity	NPD1611	Approved
0.7013	Intermediate Similarity	NPD2346	Discontinued
0.7013	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6232	Discontinued
0.7	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD7286	Phase 2
0.7	Intermediate Similarity	NPD4062	Phase 3
0.6994	Remote Similarity	NPD1465	Phase 2
0.6993	Remote Similarity	NPD1778	Approved
0.6987	Remote Similarity	NPD3892	Phase 2
0.6982	Remote Similarity	NPD7473	Discontinued
0.6981	Remote Similarity	NPD1512	Approved
0.6974	Remote Similarity	NPD6651	Approved
0.6964	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3226	Approved
0.6951	Remote Similarity	NPD2415	Discontinued
0.6946	Remote Similarity	NPD8127	Discontinued
0.6944	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3751	Discontinued
0.6937	Remote Similarity	NPD7427	Discontinued
0.6928	Remote Similarity	NPD919	Approved
0.6927	Remote Similarity	NPD4360	Phase 2
0.6927	Remote Similarity	NPD4363	Phase 3
0.6923	Remote Similarity	NPD2800	Approved
0.6918	Remote Similarity	NPD6583	Phase 3
0.6918	Remote Similarity	NPD3685	Discontinued

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