NPASS Compound

Structure

NPC14697 OpenBabel07101718222D 28 31 0 0 1 0 0 0 0 0999 V2000 2.3042 2.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9945 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4030 0.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5721 2.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7683 0.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6343 -0.6819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9023 1.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2939 2.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6343 -1.6819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4382 1.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3042 0.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0362 -0.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4382 2.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7683 -0.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0362 0.8181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9023 -0.6819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2939 1.3181 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7683 -2.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7683 -3.1819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1702 1.3181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9023 -1.6819 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 16 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 17 19 2 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 1 0 0 0 21 11 1 6 0 0 0 21 23 1 0 0 0 0 21 28 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 24 4 1 1 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.21
Volume:	408.776
LogP:	5.562
LogD:	4.526
LogS:	-6.392
# Rotatable Bonds:	6
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.489
Synthetic Accessibility Score:	4.58
Fsp3:	0.542
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:	-4.796
MDCK Permeability:	2.0322526324889623e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.7121810913086%
Volume Distribution (VD):	0.978
Pgp-substrate:	1.9649635553359985%

ADMET: Metabolism

CYP1A2-inhibitor:	0.449
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.554
CYP2C19-substrate:	0.614
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.535
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	9.705
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.483
Drug-inuced Liver Injury (DILI):	0.466
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.741
Carcinogencity:	0.026
Eye Corrosion:	0.007
Eye Irritation:	0.314
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC14697

Natural Product ID:	NPC14697
*Common Name:**	Farnesiferol C
IUPAC Name:	7-[(E)-3-methyl-5-[(1R,3R,4S)-2,2,4-trimethyl-7-oxabicyclo[2.2.1]heptan-3-yl]pent-2-enoxy]chromen-2-one
Synonyms:	Farnesiferol C
Standard InCHIKey:	OCHZHKVSLMBEJP-QYQYHAIPSA-N
Standard InCHI:	InChI=1S/C24H30O4/c1-16(5-9-20-23(2,3)21-11-13-24(20,4)28-21)12-14-26-18-8-6-17-7-10-22(25)27-19(17)15-18/h6-8,10,12,15,20-21H,5,9,11,13-14H2,1-4H3/b16-12+/t20-,21-,24+/m1/s1
SMILES:	C/C(=CCOc1ccc2ccc(=O)oc2c1)/CC[C@@H]1C(C)(C)[C@H]2CC[C@]1(C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL177697
PubChem CID:	15559239
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO10996	Ferula assa-foetida	Species	Apiaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5372	Individual Protein	Squalene-hopene cyclase	Alicyclobacillus acidocaldarius subsp. acidocaldarius (strain ATCC27009 / DSM 446 / 104-1A) (Bacillus acidocaldarius)	IC50	=	7000.0	nM	PMID[450002]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	0.29	ug.mL-1	PMID[450003]
NPT742	Organism	Influenza A virus	Influenza A virus	IC90	=	0.5	ug.mL-1	PMID[450003]

☑ 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 NPC14697 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	436
0.1-0.2	1685
0.2-0.3	3125
0.3-0.4	8374
0.4-0.5	10994
0.5-0.6	5032
0.6-0.7	6649
0.7-0.8	5759
0.8-0.85	500
0.85-0.9	142
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC306365
0.9185	High Similarity	NPC283331
0.9173	High Similarity	NPC14248
0.9118	High Similarity	NPC131198
0.9104	High Similarity	NPC222036
0.9104	High Similarity	NPC7526
0.9058	High Similarity	NPC138149
0.9037	High Similarity	NPC307412
0.9037	High Similarity	NPC55149
0.9008	High Similarity	NPC234109
0.9008	High Similarity	NPC188327
0.8993	High Similarity	NPC20631
0.8993	High Similarity	NPC93640
0.8931	High Similarity	NPC471828
0.8931	High Similarity	NPC471827
0.8913	High Similarity	NPC307883
0.8881	High Similarity	NPC80170
0.8864	High Similarity	NPC101894
0.8855	High Similarity	NPC201667
0.8855	High Similarity	NPC73413
0.8855	High Similarity	NPC27671
0.8832	High Similarity	NPC472424
0.8832	High Similarity	NPC281241
0.8832	High Similarity	NPC471909
0.8832	High Similarity	NPC86892
0.8832	High Similarity	NPC471625
0.8824	High Similarity	NPC318400
0.8824	High Similarity	NPC207002
0.8824	High Similarity	NPC167111
0.8824	High Similarity	NPC471910
0.8824	High Similarity	NPC133956
0.8824	High Similarity	NPC296624
0.8806	High Similarity	NPC168710
0.8797	High Similarity	NPC289316
0.8786	High Similarity	NPC155552
0.8779	High Similarity	NPC109675
0.8779	High Similarity	NPC472518
0.8779	High Similarity	NPC273772
0.8768	High Similarity	NPC471630
0.8768	High Similarity	NPC283019
0.8768	High Similarity	NPC160727
0.8768	High Similarity	NPC177281
0.8768	High Similarity	NPC149320
0.8768	High Similarity	NPC55615
0.8768	High Similarity	NPC476455
0.8768	High Similarity	NPC128529
0.8759	High Similarity	NPC198381
0.8759	High Similarity	NPC166672
0.8759	High Similarity	NPC18804
0.8759	High Similarity	NPC127888
0.8759	High Similarity	NPC84894
0.8759	High Similarity	NPC74655
0.8759	High Similarity	NPC260265
0.8759	High Similarity	NPC253574
0.8759	High Similarity	NPC100986
0.8759	High Similarity	NPC164269
0.8759	High Similarity	NPC267412
0.8759	High Similarity	NPC47163
0.8759	High Similarity	NPC287182
0.8759	High Similarity	NPC98179
0.8759	High Similarity	NPC195343
0.8759	High Similarity	NPC319859
0.8731	High Similarity	NPC472519
0.8731	High Similarity	NPC199204
0.8731	High Similarity	NPC185066
0.8722	High Similarity	NPC163248
0.8722	High Similarity	NPC471826
0.8702	High Similarity	NPC96286
0.8702	High Similarity	NPC248429
0.8696	High Similarity	NPC469675
0.8696	High Similarity	NPC33986
0.8692	High Similarity	NPC235190
0.8692	High Similarity	NPC163200
0.8692	High Similarity	NPC180006
0.8686	High Similarity	NPC31849
0.8686	High Similarity	NPC163557
0.8652	High Similarity	NPC472523
0.8623	High Similarity	NPC62366
0.8623	High Similarity	NPC180716
0.8623	High Similarity	NPC224475
0.8623	High Similarity	NPC213173
0.8603	High Similarity	NPC113098
0.8601	High Similarity	NPC251372
0.8593	High Similarity	NPC157212
0.8593	High Similarity	NPC60704
0.8593	High Similarity	NPC139595
0.8593	High Similarity	NPC293642
0.8571	High Similarity	NPC111347
0.8571	High Similarity	NPC291899
0.8571	High Similarity	NPC155963
0.8562	High Similarity	NPC146388
0.8561	High Similarity	NPC472525
0.8551	High Similarity	NPC469955
0.8551	High Similarity	NPC469952
0.8542	High Similarity	NPC108994
0.8542	High Similarity	NPC106126
0.854	High Similarity	NPC29734
0.854	High Similarity	NPC272650
0.854	High Similarity	NPC267336
0.8538	High Similarity	NPC281356
0.8538	High Similarity	NPC298796
0.8521	High Similarity	NPC287286
0.8519	High Similarity	NPC121740
0.8519	High Similarity	NPC258567
0.8519	High Similarity	NPC224774
0.8511	High Similarity	NPC211110
0.8511	High Similarity	NPC151946
0.8511	High Similarity	NPC279573
0.8503	High Similarity	NPC146014
0.85	High Similarity	NPC38099
0.85	High Similarity	NPC26954
0.8496	Intermediate Similarity	NPC290605
0.8496	Intermediate Similarity	NPC173350
0.8496	Intermediate Similarity	NPC154176
0.8496	Intermediate Similarity	NPC315807
0.8496	Intermediate Similarity	NPC50720
0.8489	Intermediate Similarity	NPC326600
0.8489	Intermediate Similarity	NPC50896
0.8489	Intermediate Similarity	NPC204353
0.8485	Intermediate Similarity	NPC144418
0.8478	Intermediate Similarity	NPC469956
0.8478	Intermediate Similarity	NPC19157
0.8478	Intermediate Similarity	NPC194277
0.8467	Intermediate Similarity	NPC19242
0.8462	Intermediate Similarity	NPC152306
0.8462	Intermediate Similarity	NPC96705
0.8462	Intermediate Similarity	NPC265547
0.8456	Intermediate Similarity	NPC469453
0.8451	Intermediate Similarity	NPC312881
0.844	Intermediate Similarity	NPC153818
0.844	Intermediate Similarity	NPC232246
0.8429	Intermediate Similarity	NPC229128
0.8425	Intermediate Similarity	NPC286038
0.8421	Intermediate Similarity	NPC257188
0.8421	Intermediate Similarity	NPC150214
0.8421	Intermediate Similarity	NPC13007
0.8417	Intermediate Similarity	NPC54503
0.8417	Intermediate Similarity	NPC55147
0.8417	Intermediate Similarity	NPC472524
0.8417	Intermediate Similarity	NPC469449
0.8414	Intermediate Similarity	NPC469701
0.8406	Intermediate Similarity	NPC66430
0.8406	Intermediate Similarity	NPC37009
0.8392	Intermediate Similarity	NPC195357
0.8392	Intermediate Similarity	NPC152771
0.8382	Intermediate Similarity	NPC243688
0.8369	Intermediate Similarity	NPC224543
0.8369	Intermediate Similarity	NPC78746
0.8369	Intermediate Similarity	NPC188380
0.8367	Intermediate Similarity	NPC66991
0.8333	Intermediate Similarity	NPC473290
0.8333	Intermediate Similarity	NPC471504
0.831	Intermediate Similarity	NPC294456
0.831	Intermediate Similarity	NPC281014
0.831	Intermediate Similarity	NPC184861
0.831	Intermediate Similarity	NPC471068
0.831	Intermediate Similarity	NPC212124
0.831	Intermediate Similarity	NPC471069
0.831	Intermediate Similarity	NPC225106
0.8308	Intermediate Similarity	NPC128633
0.8299	Intermediate Similarity	NPC296377
0.8298	Intermediate Similarity	NPC61499
0.8296	Intermediate Similarity	NPC294156
0.8296	Intermediate Similarity	NPC256015
0.8289	Intermediate Similarity	NPC470625
0.8288	Intermediate Similarity	NPC43716
0.8288	Intermediate Similarity	NPC101255
0.8288	Intermediate Similarity	NPC475719
0.8286	Intermediate Similarity	NPC36437
0.8286	Intermediate Similarity	NPC241341
0.8286	Intermediate Similarity	NPC291551
0.8286	Intermediate Similarity	NPC205797
0.8286	Intermediate Similarity	NPC142563
0.8286	Intermediate Similarity	NPC2363
0.8286	Intermediate Similarity	NPC469965
0.8286	Intermediate Similarity	NPC233018
0.8286	Intermediate Similarity	NPC1220
0.8286	Intermediate Similarity	NPC141822
0.8286	Intermediate Similarity	NPC241165
0.8286	Intermediate Similarity	NPC83535
0.8276	Intermediate Similarity	NPC119640
0.8276	Intermediate Similarity	NPC183646
0.8252	Intermediate Similarity	NPC270256
0.8252	Intermediate Similarity	NPC47040
0.8252	Intermediate Similarity	NPC471070
0.8252	Intermediate Similarity	NPC471071
0.8252	Intermediate Similarity	NPC278600
0.8252	Intermediate Similarity	NPC35501
0.8252	Intermediate Similarity	NPC471072
0.8252	Intermediate Similarity	NPC37428
0.8252	Intermediate Similarity	NPC144512
0.8252	Intermediate Similarity	NPC137262
0.8243	Intermediate Similarity	NPC169510
0.8235	Intermediate Similarity	NPC93219
0.8235	Intermediate Similarity	NPC202594
0.8235	Intermediate Similarity	NPC232692
0.8235	Intermediate Similarity	NPC244495
0.8231	Intermediate Similarity	NPC475872
0.8227	Intermediate Similarity	NPC131950
0.8224	Intermediate Similarity	NPC117154

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 NPC14697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	947
0.2-0.3	1653
0.3-0.4	2698
0.4-0.5	2046
0.5-0.6	1000
0.6-0.7	309
0.7-0.8	103
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8286	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD5124	Phase 1
0.8074	Intermediate Similarity	NPD422	Phase 1
0.7959	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3748	Approved
0.7852	Intermediate Similarity	NPD5691	Approved
0.7801	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4140	Approved
0.7697	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1296	Phase 2
0.7687	Intermediate Similarity	NPD2796	Approved
0.7676	Intermediate Similarity	NPD4908	Phase 1
0.7651	Intermediate Similarity	NPD1652	Phase 2
0.7651	Intermediate Similarity	NPD1243	Approved
0.7647	Intermediate Similarity	NPD920	Approved
0.7616	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3750	Approved
0.758	Intermediate Similarity	NPD7819	Suspended
0.7554	Intermediate Similarity	NPD1610	Phase 2
0.7538	Intermediate Similarity	NPD3134	Approved
0.7536	Intermediate Similarity	NPD4626	Approved
0.7535	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7482	Intermediate Similarity	NPD3496	Discontinued
0.7467	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4060	Phase 1
0.7465	Intermediate Similarity	NPD3267	Approved
0.7465	Intermediate Similarity	NPD2797	Approved
0.7465	Intermediate Similarity	NPD3266	Approved
0.7463	Intermediate Similarity	NPD5535	Approved
0.7462	Intermediate Similarity	NPD9697	Approved
0.7447	Intermediate Similarity	NPD5327	Phase 3
0.7447	Intermediate Similarity	NPD4749	Approved
0.74	Intermediate Similarity	NPD5762	Approved
0.74	Intermediate Similarity	NPD5763	Approved
0.74	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6002	Phase 3
0.74	Intermediate Similarity	NPD6004	Phase 3
0.74	Intermediate Similarity	NPD6005	Phase 3
0.74	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD8032	Phase 2
0.7391	Intermediate Similarity	NPD919	Approved
0.7391	Intermediate Similarity	NPD1548	Phase 1
0.7379	Intermediate Similarity	NPD4625	Phase 3
0.7375	Intermediate Similarity	NPD4965	Approved
0.7375	Intermediate Similarity	NPD4966	Approved
0.7375	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD1653	Approved
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7358	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6273	Approved
0.7348	Intermediate Similarity	NPD1358	Approved
0.7346	Intermediate Similarity	NPD5494	Approved
0.7338	Intermediate Similarity	NPD5585	Approved
0.7338	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD3268	Approved
0.7325	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6832	Phase 2
0.7305	Intermediate Similarity	NPD1611	Approved
0.7301	Intermediate Similarity	NPD7199	Phase 2
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD2533	Approved
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1778	Approved
0.7284	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7256	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD7466	Approved
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7241	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD7411	Suspended
0.723	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3749	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7212	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8127	Discontinued
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD37	Approved
0.7181	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7157	Approved
0.7163	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD3225	Approved
0.7153	Intermediate Similarity	NPD6696	Suspended
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD7095	Approved
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6353	Approved
0.7125	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1549	Phase 2
0.7124	Intermediate Similarity	NPD2424	Discontinued
0.7114	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1613	Approved
0.7105	Intermediate Similarity	NPD1551	Phase 2
0.7099	Intermediate Similarity	NPD3817	Phase 2
0.7099	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5403	Approved
0.7083	Intermediate Similarity	NPD4359	Approved
0.7078	Intermediate Similarity	NPD2800	Approved
0.7076	Intermediate Similarity	NPD7549	Discontinued
0.7071	Intermediate Similarity	NPD7644	Approved
0.707	Intermediate Similarity	NPD5401	Approved
0.707	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4481	Phase 3
0.7063	Intermediate Similarity	NPD3705	Approved
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6667	Approved
0.7051	Intermediate Similarity	NPD6666	Approved
0.7039	Intermediate Similarity	NPD1510	Phase 2
0.7039	Intermediate Similarity	NPD4308	Phase 3
0.7037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4110	Phase 3
0.7032	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3892	Phase 2
0.7029	Intermediate Similarity	NPD1241	Discontinued
0.7027	Intermediate Similarity	NPD3027	Phase 3
0.7014	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD2237	Approved
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6994	Remote Similarity	NPD4288	Approved
0.6994	Remote Similarity	NPD5402	Approved
0.6993	Remote Similarity	NPD2438	Suspended
0.6993	Remote Similarity	NPD2935	Discontinued
0.6982	Remote Similarity	NPD7228	Approved
0.698	Remote Similarity	NPD6798	Discontinued
0.6974	Remote Similarity	NPD7097	Phase 1
0.6968	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4380	Phase 2
0.6954	Remote Similarity	NPD4340	Discontinued
0.6951	Remote Similarity	NPD3882	Suspended
0.6948	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1281	Approved
0.6939	Remote Similarity	NPD1019	Discontinued
0.6933	Remote Similarity	NPD4870	Approved
0.6923	Remote Similarity	NPD7003	Approved
0.6919	Remote Similarity	NPD6559	Discontinued
0.6912	Remote Similarity	NPD2684	Approved
0.6909	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2157	Approved
0.6906	Remote Similarity	NPD5283	Phase 1
0.6897	Remote Similarity	NPD9717	Approved
0.6892	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3018	Phase 2
0.6887	Remote Similarity	NPD1240	Approved
0.6886	Remote Similarity	NPD1247	Approved
0.6883	Remote Similarity	NPD4476	Approved
0.6883	Remote Similarity	NPD4477	Approved
0.6882	Remote Similarity	NPD3818	Discontinued
0.6871	Remote Similarity	NPD1934	Approved
0.6867	Remote Similarity	NPD3764	Approved
0.6863	Remote Similarity	NPD2200	Suspended
0.6849	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7843	Approved
0.6832	Remote Similarity	NPD4210	Discontinued
0.6829	Remote Similarity	NPD5760	Phase 2
0.6829	Remote Similarity	NPD5761	Phase 2
0.6828	Remote Similarity	NPD1091	Approved
0.6824	Remote Similarity	NPD4624	Approved
0.6821	Remote Similarity	NPD7240	Approved
0.6818	Remote Similarity	NPD8434	Phase 2
0.6809	Remote Similarity	NPD6671	Approved
0.6807	Remote Similarity	NPD6971	Discontinued
0.6805	Remote Similarity	NPD3926	Phase 2
0.6803	Remote Similarity	NPD1283	Approved
0.6803	Remote Similarity	NPD1876	Approved
0.6797	Remote Similarity	NPD1607	Approved
0.6797	Remote Similarity	NPD4097	Suspended
0.6797	Remote Similarity	NPD6653	Approved
0.6792	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7213	Phase 3
0.6792	Remote Similarity	NPD7212	Phase 2
0.679	Remote Similarity	NPD3226	Approved
0.6786	Remote Similarity	NPD6959	Discontinued
0.6781	Remote Similarity	NPD3972	Approved
0.6781	Remote Similarity	NPD2981	Phase 2
0.6779	Remote Similarity	NPD5736	Approved
0.6776	Remote Similarity	NPD2238	Phase 2
0.6774	Remote Similarity	NPD2531	Phase 2
0.6766	Remote Similarity	NPD5537	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