NPASS Compound

Structure

NPC106126 OpenBabel07101718322D 30 35 0 0 1 0 0 0 0 0999 V2000 5.0733 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7210 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8549 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2072 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9889 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -4.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -3.1691 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 13 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 1 1 6 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 2 1 6 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 26 2 0 0 0 0 15 29 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 17 1 6 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 27 1 6 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.16
Volume:	412.477
LogP:	6.153
LogD:	4.325
LogS:	-6.136
# Rotatable Bonds:	1
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.38
Fsp3:	0.4
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:	-4.885
MDCK Permeability:	3.241933882236481e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	86.64238739013672%
Volume Distribution (VD):	1.127
Pgp-substrate:	8.189805030822754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.196
CYP1A2-substrate:	0.6
CYP2C19-inhibitor:	0.554
CYP2C19-substrate:	0.322
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.455
CYP3A4-inhibitor:	0.223
CYP3A4-substrate:	0.424

ADMET: Excretion

Clearance (CL):	4.054
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.782
Skin Sensitization:	0.132
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.282

Download Data

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

Natural Product: NPC106126

Natural Product ID:	NPC106126
*Common Name:**	NDJILOHYAHLIPO-OVTDJOJUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NDJILOHYAHLIPO-OVTDJOJUSA-N
Standard InCHI:	InChI=1S/C25H24O5/c1-11-12(2)28-23-17-19-24(25(19,3)4)30-21(17)16-14(13-8-6-5-7-9-13)10-15(26)29-22(16)18(23)20(11)27/h5-12,19-20,24,27H,1-4H3/t11-,12+,19+,20-,24-/m0/s1
SMILES:	C[C@H]1Oc2c3c(O[C@H]4[C@@H]3C4(C)C)c3c(c2[C@H]([C@H]1C)O)oc(=O)cc3c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL335955
PubChem CID:	455255
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003652] Pyranoneoflavonoids

*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	1

Activity Type	# Activity
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	=	70000.0	nM	PMID[537083]

☑ 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 NPC106126 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	373
0.1-0.2	1584
0.2-0.3	3264
0.3-0.4	8026
0.4-0.5	10993
0.5-0.6	4739
0.6-0.7	6133
0.7-0.8	5836
0.8-0.85	1407
0.85-0.9	318
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108994
0.9143	High Similarity	NPC278600
0.9143	High Similarity	NPC37428
0.9143	High Similarity	NPC35501
0.9143	High Similarity	NPC47040
0.9143	High Similarity	NPC144512
0.9143	High Similarity	NPC137262
0.9014	High Similarity	NPC138149
0.8951	High Similarity	NPC93640
0.8951	High Similarity	NPC20631
0.8936	High Similarity	NPC131198
0.8921	High Similarity	NPC291551
0.8921	High Similarity	NPC205797
0.8921	High Similarity	NPC469965
0.8921	High Similarity	NPC31849
0.8921	High Similarity	NPC142563
0.8921	High Similarity	NPC241165
0.8921	High Similarity	NPC141822
0.8921	High Similarity	NPC1220
0.8897	High Similarity	NPC475719
0.8897	High Similarity	NPC43716
0.8897	High Similarity	NPC469701
0.8897	High Similarity	NPC101255
0.8873	High Similarity	NPC279573
0.8857	High Similarity	NPC115335
0.8857	High Similarity	NPC225696
0.8857	High Similarity	NPC223008
0.8857	High Similarity	NPC296915
0.8857	High Similarity	NPC131950
0.8857	High Similarity	NPC198154
0.8857	High Similarity	NPC97834
0.8786	High Similarity	NPC163557
0.8786	High Similarity	NPC469955
0.8786	High Similarity	NPC469952
0.8777	High Similarity	NPC280653
0.8777	High Similarity	NPC207892
0.8777	High Similarity	NPC300875
0.8777	High Similarity	NPC129784
0.8777	High Similarity	NPC12875
0.8777	High Similarity	NPC206224
0.8777	High Similarity	NPC17343
0.8777	High Similarity	NPC118114
0.8777	High Similarity	NPC476166
0.8777	High Similarity	NPC196765
0.8777	High Similarity	NPC129106
0.8777	High Similarity	NPC268917
0.8777	High Similarity	NPC236014
0.8777	High Similarity	NPC150011
0.8777	High Similarity	NPC164574
0.8777	High Similarity	NPC228369
0.875	High Similarity	NPC287286
0.875	High Similarity	NPC5155
0.875	High Similarity	NPC195357
0.875	High Similarity	NPC152771
0.8741	High Similarity	NPC211110
0.8732	High Similarity	NPC26954
0.8732	High Similarity	NPC38099
0.8723	High Similarity	NPC326600
0.8723	High Similarity	NPC50896
0.8723	High Similarity	NPC204353
0.8714	High Similarity	NPC194277
0.8714	High Similarity	NPC13005
0.8705	High Similarity	NPC470225
0.8705	High Similarity	NPC32463
0.8705	High Similarity	NPC27187
0.8681	High Similarity	NPC312881
0.8671	High Similarity	NPC153818
0.8671	High Similarity	NPC184861
0.8671	High Similarity	NPC294456
0.8671	High Similarity	NPC232246
0.8671	High Similarity	NPC212124
0.8671	High Similarity	NPC306365
0.8671	High Similarity	NPC225106
0.8671	High Similarity	NPC281014
0.8643	High Similarity	NPC244888
0.8643	High Similarity	NPC118683
0.8643	High Similarity	NPC181497
0.8643	High Similarity	NPC271945
0.8643	High Similarity	NPC164804
0.8643	High Similarity	NPC293203
0.8643	High Similarity	NPC68205
0.8643	High Similarity	NPC211413
0.8639	High Similarity	NPC71739
0.8621	High Similarity	NPC155552
0.8611	High Similarity	NPC475836
0.8611	High Similarity	NPC151946
0.8601	High Similarity	NPC18189
0.8601	High Similarity	NPC20829
0.8601	High Similarity	NPC262585
0.8601	High Similarity	NPC188380
0.8601	High Similarity	NPC224543
0.8601	High Similarity	NPC78746
0.8592	High Similarity	NPC180716
0.8592	High Similarity	NPC213173
0.8592	High Similarity	NPC62366
0.8592	High Similarity	NPC224475
0.8591	High Similarity	NPC169510
0.8582	High Similarity	NPC19157
0.8582	High Similarity	NPC469956
0.8581	High Similarity	NPC471608
0.8571	High Similarity	NPC471824
0.8561	High Similarity	NPC38664
0.8561	High Similarity	NPC139595
0.8561	High Similarity	NPC53986
0.8561	High Similarity	NPC39064
0.8561	High Similarity	NPC293642
0.8561	High Similarity	NPC274717
0.8561	High Similarity	NPC60704
0.8561	High Similarity	NPC47283
0.8542	High Similarity	NPC155963
0.8542	High Similarity	NPC14697
0.8533	High Similarity	NPC146388
0.8531	High Similarity	NPC471909
0.8531	High Similarity	NPC471625
0.8531	High Similarity	NPC33986
0.8531	High Similarity	NPC472525
0.8531	High Similarity	NPC472424
0.8531	High Similarity	NPC281241
0.8531	High Similarity	NPC86892
0.8523	High Similarity	NPC296377
0.8521	High Similarity	NPC133956
0.8521	High Similarity	NPC318400
0.8521	High Similarity	NPC296624
0.8521	High Similarity	NPC471910
0.8521	High Similarity	NPC207002
0.8521	High Similarity	NPC77196
0.8521	High Similarity	NPC85435
0.8521	High Similarity	NPC167111
0.8514	High Similarity	NPC226722
0.8514	High Similarity	NPC295696
0.8511	High Similarity	NPC66430
0.8511	High Similarity	NPC37009
0.8511	High Similarity	NPC250727
0.85	High Similarity	NPC168710
0.85	High Similarity	NPC93962
0.8497	Intermediate Similarity	NPC268484
0.8489	Intermediate Similarity	NPC121740
0.8489	Intermediate Similarity	NPC258567
0.8489	Intermediate Similarity	NPC224774
0.8487	Intermediate Similarity	NPC290671
0.8477	Intermediate Similarity	NPC103116
0.8477	Intermediate Similarity	NPC146014
0.8472	Intermediate Similarity	NPC476455
0.8472	Intermediate Similarity	NPC471630
0.8472	Intermediate Similarity	NPC149320
0.8472	Intermediate Similarity	NPC128529
0.8472	Intermediate Similarity	NPC283331
0.8472	Intermediate Similarity	NPC283019
0.8472	Intermediate Similarity	NPC55615
0.8472	Intermediate Similarity	NPC160727
0.8472	Intermediate Similarity	NPC177281
0.8467	Intermediate Similarity	NPC142863
0.8462	Intermediate Similarity	NPC98179
0.8462	Intermediate Similarity	NPC74655
0.8462	Intermediate Similarity	NPC307412
0.8462	Intermediate Similarity	NPC253574
0.8462	Intermediate Similarity	NPC198381
0.8462	Intermediate Similarity	NPC124085
0.8462	Intermediate Similarity	NPC319859
0.8462	Intermediate Similarity	NPC164269
0.8462	Intermediate Similarity	NPC84894
0.8462	Intermediate Similarity	NPC127888
0.8462	Intermediate Similarity	NPC166672
0.8462	Intermediate Similarity	NPC100986
0.8462	Intermediate Similarity	NPC47163
0.8462	Intermediate Similarity	NPC18804
0.8462	Intermediate Similarity	NPC195343
0.8462	Intermediate Similarity	NPC117048
0.8462	Intermediate Similarity	NPC260265
0.8462	Intermediate Similarity	NPC55149
0.8462	Intermediate Similarity	NPC267412
0.8462	Intermediate Similarity	NPC287182
0.8451	Intermediate Similarity	NPC14248
0.8446	Intermediate Similarity	NPC36732
0.844	Intermediate Similarity	NPC80170
0.8431	Intermediate Similarity	NPC223720
0.8429	Intermediate Similarity	NPC219923
0.8429	Intermediate Similarity	NPC199204
0.8429	Intermediate Similarity	NPC469453
0.8429	Intermediate Similarity	NPC185066
0.8425	Intermediate Similarity	NPC71903
0.8421	Intermediate Similarity	NPC474735
0.8417	Intermediate Similarity	NPC283049
0.8417	Intermediate Similarity	NPC276212
0.8417	Intermediate Similarity	NPC230479
0.8417	Intermediate Similarity	NPC471215
0.8417	Intermediate Similarity	NPC26879
0.8417	Intermediate Similarity	NPC188327
0.8417	Intermediate Similarity	NPC50315
0.8417	Intermediate Similarity	NPC262573
0.8417	Intermediate Similarity	NPC234109
0.8414	Intermediate Similarity	NPC474687
0.8406	Intermediate Similarity	NPC256015
0.8406	Intermediate Similarity	NPC294156
0.84	Intermediate Similarity	NPC476347
0.84	Intermediate Similarity	NPC471764
0.84	Intermediate Similarity	NPC87950
0.8392	Intermediate Similarity	NPC92805
0.8392	Intermediate Similarity	NPC7526
0.8392	Intermediate Similarity	NPC83535

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 NPC106126 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	939
0.2-0.3	1650
0.3-0.4	2581
0.4-0.5	2142
0.5-0.6	1032
0.6-0.7	337
0.7-0.8	123
0.8-0.85	22
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8921	High Similarity	NPD5124	Phase 1
0.8921	High Similarity	NPD5123	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD4908	Phase 1
0.8058	Intermediate Similarity	NPD1610	Phase 2
0.8058	Intermediate Similarity	NPD422	Phase 1
0.8013	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1652	Phase 2
0.7857	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2797	Approved
0.7829	Intermediate Similarity	NPD3750	Approved
0.7829	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7411	Suspended
0.7771	Intermediate Similarity	NPD5844	Phase 1
0.777	Intermediate Similarity	NPD1548	Phase 1
0.775	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6005	Phase 3
0.7748	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6002	Phase 3
0.7748	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6004	Phase 3
0.7742	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2861	Phase 2
0.7722	Intermediate Similarity	NPD4380	Phase 2
0.7703	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4140	Approved
0.7703	Intermediate Similarity	NPD1613	Approved
0.7702	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7819	Suspended
0.7687	Intermediate Similarity	NPD3268	Approved
0.7654	Intermediate Similarity	NPD7075	Discontinued
0.7639	Intermediate Similarity	NPD3225	Approved
0.7625	Intermediate Similarity	NPD6801	Discontinued
0.7619	Intermediate Similarity	NPD4625	Phase 3
0.7616	Intermediate Similarity	NPD3748	Approved
0.7616	Intermediate Similarity	NPD7033	Discontinued
0.7597	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD1653	Approved
0.7584	Intermediate Similarity	NPD4060	Phase 1
0.7578	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD37	Approved
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6666	Approved
0.75	Intermediate Similarity	NPD6667	Approved
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7229	Phase 3
0.7468	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD1549	Phase 2
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5494	Approved
0.7451	Intermediate Similarity	NPD2796	Approved
0.7448	Intermediate Similarity	NPD4749	Approved
0.7439	Intermediate Similarity	NPD3749	Approved
0.7438	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6559	Discontinued
0.7421	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD5403	Approved
0.7419	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2800	Approved
0.7417	Intermediate Similarity	NPD6355	Discontinued
0.7415	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2534	Approved
0.7405	Intermediate Similarity	NPD2533	Approved
0.7405	Intermediate Similarity	NPD2532	Approved
0.7397	Intermediate Similarity	NPD8651	Approved
0.7391	Intermediate Similarity	NPD6599	Discontinued
0.7384	Intermediate Similarity	NPD7549	Discontinued
0.7383	Intermediate Similarity	NPD3027	Phase 3
0.7365	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8455	Phase 2
0.7361	Intermediate Similarity	NPD3496	Discontinued
0.7355	Intermediate Similarity	NPD2424	Discontinued
0.7347	Intermediate Similarity	NPD3267	Approved
0.7347	Intermediate Similarity	NPD3266	Approved
0.7343	Intermediate Similarity	NPD5585	Approved
0.7342	Intermediate Similarity	NPD7212	Phase 2
0.7342	Intermediate Similarity	NPD7213	Phase 3
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.7338	Intermediate Similarity	NPD5535	Approved
0.732	Intermediate Similarity	NPD7097	Phase 1
0.7317	Intermediate Similarity	NPD5402	Approved
0.7315	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7305	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD8127	Discontinued
0.7301	Intermediate Similarity	NPD1934	Approved
0.7296	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5401	Approved
0.7296	Intermediate Similarity	NPD7447	Phase 1
0.7294	Intermediate Similarity	NPD7228	Approved
0.7292	Intermediate Similarity	NPD4626	Approved
0.729	Intermediate Similarity	NPD5763	Approved
0.729	Intermediate Similarity	NPD5762	Approved
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6234	Discontinued
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5058	Phase 3
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD5960	Phase 3
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD5588	Approved
0.7261	Intermediate Similarity	NPD7466	Approved
0.7261	Intermediate Similarity	NPD7003	Approved
0.7244	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6799	Approved
0.7226	Intermediate Similarity	NPD1551	Phase 2
0.7226	Intermediate Similarity	NPD2935	Discontinued
0.7222	Intermediate Similarity	NPD5691	Approved
0.7219	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD1296	Phase 2
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7208	Intermediate Similarity	NPD4536	Approved
0.7208	Intermediate Similarity	NPD4538	Approved
0.7208	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6674	Discontinued
0.7193	Intermediate Similarity	NPD3818	Discontinued
0.7192	Intermediate Similarity	NPD1091	Approved
0.719	Intermediate Similarity	NPD4340	Discontinued
0.7184	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD7095	Approved
0.7151	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.711	Intermediate Similarity	NPD7074	Phase 3
0.711	Intermediate Similarity	NPD7472	Approved
0.7108	Intermediate Similarity	NPD4288	Approved
0.7105	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4359	Approved
0.7086	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5735	Approved
0.7075	Intermediate Similarity	NPD1611	Approved
0.707	Intermediate Similarity	NPD2346	Discontinued
0.707	Intermediate Similarity	NPD7266	Discontinued
0.7069	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6797	Phase 2
0.7063	Intermediate Similarity	NPD7157	Approved
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7055	Intermediate Similarity	NPD1778	Approved
0.7048	Intermediate Similarity	NPD2801	Approved
0.7048	Intermediate Similarity	NPD1465	Phase 2
0.7047	Intermediate Similarity	NPD6696	Suspended
0.7044	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3892	Phase 2
0.7035	Intermediate Similarity	NPD7473	Discontinued
0.7034	Intermediate Similarity	NPD7741	Discontinued
0.7029	Intermediate Similarity	NPD7251	Discontinued
0.7029	Intermediate Similarity	NPD7240	Approved
0.7027	Intermediate Similarity	NPD1608	Approved
0.7019	Intermediate Similarity	NPD1511	Approved
0.7013	Intermediate Similarity	NPD1240	Approved
0.7012	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD4477	Approved
0.7006	Intermediate Similarity	NPD4476	Approved
0.6989	Remote Similarity	NPD7808	Phase 3
0.6982	Remote Similarity	NPD919	Approved
0.698	Remote Similarity	NPD5327	Phase 3
0.698	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4363	Phase 3
0.6978	Remote Similarity	NPD4360	Phase 2
0.6974	Remote Similarity	NPD6832	Phase 2
0.6964	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD5710	Approved
0.6959	Remote Similarity	NPD5711	Approved
0.6948	Remote Similarity	NPD4870	Approved
0.6948	Remote Similarity	NPD8032	Phase 2
0.6939	Remote Similarity	NPD5125	Phase 3
0.6939	Remote Similarity	NPD5126	Approved
0.6937	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4110	Phase 3
0.6933	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8434	Phase 2
0.6923	Remote Similarity	NPD4097	Suspended
0.6923	Remote Similarity	NPD6651	Approved
0.6923	Remote Similarity	NPD6653	Approved
0.6923	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD1894	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