NPASS Compound

Structure

CID709 OpenBabel06191715322D 35 40 0 0 1 0 0 0 0 0999 V2000 -8.2147 -3.0145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7410 0.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1238 0.0158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0952 -1.9609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2464 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8499 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3970 0.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2464 0.4901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0796 -1.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6988 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6713 -1.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5477 1.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0113 -2.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9444 -0.4915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5482 -0.4904 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7396 -1.4007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0958 -0.9812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3975 -0.9808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5481 0.4904 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8762 -0.7946 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6990 1.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8494 -0.4904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5362 -0.4423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2464 -0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6988 0.9808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8494 0.4904 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3996 -1.0483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5280 1.4709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5651 2.4611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8657 0.4803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2645 0.2131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6045 -0.1392 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 14 1 0 0 0 0 4 5 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 7 2 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 26 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 17 1 0 0 0 0 12 29 1 0 0 0 0 13 27 1 0 0 0 0 13 30 1 0 0 0 0 14 17 2 0 0 0 0 15 2 1 1 0 0 0 15 18 1 0 0 0 0 16 11 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 6 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 21 15 1 1 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 31 2 0 0 0 0 23 28 1 6 0 0 0 23 32 1 0 0 0 0 24 28 1 6 0 0 0 24 35 1 0 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.44
Volume:	579.813
LogP:	10.842
LogD:	5.289
LogS:	-3.834
# Rotatable Bonds:	25
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.139
Synthetic Accessibility Score:	2.27
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.377
MDCK Permeability:	5.351570962375263e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.095
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	100.13263702392578%
Volume Distribution (VD):	4.06
Pgp-substrate:	0.6106456518173218%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.242
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.759
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.051

ADMET: Excretion

Clearance (CL):	4.437
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.942
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.325
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.324
Skin Sensitization:	0.974
Carcinogencity:	0.027
Eye Corrosion:	0.004
Eye Irritation:	0.173
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC709

Natural Product ID:	NPC709
*Common Name:**	FJMXKFSOKLFYRC-CKNDUULBSA-N
IUPAC Name:	n.a.
Synonyms:	19-Hydroxywithaferin A
Standard InCHIKey:	FJMXKFSOKLFYRC-CKNDUULBSA-N
Standard InCHI:	InChI=1S/C28H38O7/c1-14-10-21(34-25(33)17(14)12-29)15(2)18-4-5-19-16-11-24-28(35-24)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h6-7,15-16,18-21,23-24,29-30,32H,4-5,8-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]4[C@@]5([C@H](C=CC(=O)[C@]5(CO)[C@H]3CC[C@]12C)O)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934449
PubChem CID:	56649343
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	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	10

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[523999]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	5100.0	nM	PMID[523999]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	5300.0	nM	PMID[524000]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	1600.0	nM	PMID[524000]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1500.0	nM	PMID[524000]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5300.0	nM	PMID[523999]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3300.0	nM	PMID[523999]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[523999]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1700.0	nM	PMID[524000]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3100.0	nM	PMID[524000]

☑ 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 NPC709 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	231
0.1-0.2	1287
0.2-0.3	3807
0.3-0.4	7391
0.4-0.5	12940
0.5-0.6	6920
0.6-0.7	6708
0.7-0.8	3049
0.8-0.85	255
0.85-0.9	54
0.9-0.95	41
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC50774
0.9907	High Similarity	NPC140055
0.9907	High Similarity	NPC286528
0.9907	High Similarity	NPC167606
0.9907	High Similarity	NPC20302
0.9818	High Similarity	NPC474370
0.973	High Similarity	NPC67569
0.9727	High Similarity	NPC264954
0.9725	High Similarity	NPC183580
0.9725	High Similarity	NPC470493
0.9725	High Similarity	NPC312824
0.9725	High Similarity	NPC470492
0.9643	High Similarity	NPC88326
0.9643	High Similarity	NPC23786
0.9643	High Similarity	NPC153700
0.9643	High Similarity	NPC470265
0.963	High Similarity	NPC122056
0.9558	High Similarity	NPC469789
0.9541	High Similarity	NPC147912
0.9541	High Similarity	NPC67259
0.9474	High Similarity	NPC8374
0.9459	High Similarity	NPC186525
0.9391	High Similarity	NPC293112
0.9375	High Similarity	NPC473274
0.9304	High Similarity	NPC8369
0.9304	High Similarity	NPC3381
0.9304	High Similarity	NPC470494
0.9279	High Similarity	NPC270929
0.9217	High Similarity	NPC11895
0.9211	High Similarity	NPC473256
0.9211	High Similarity	NPC470878
0.9204	High Similarity	NPC61520
0.9196	High Similarity	NPC243065
0.9153	High Similarity	NPC473593
0.9138	High Similarity	NPC81736
0.9138	High Similarity	NPC172154
0.913	High Similarity	NPC170538
0.9115	High Similarity	NPC329736
0.9107	High Similarity	NPC64318
0.9091	High Similarity	NPC474315
0.906	High Similarity	NPC473635
0.9018	High Similarity	NPC284915
0.9009	High Similarity	NPC191620
0.9	High Similarity	NPC29133
0.9	High Similarity	NPC231240
0.8926	High Similarity	NPC316915
0.8919	High Similarity	NPC470961
0.8899	High Similarity	NPC91034
0.8879	High Similarity	NPC46570
0.887	High Similarity	NPC473270
0.886	High Similarity	NPC476965
0.886	High Similarity	NPC470959
0.8839	High Similarity	NPC236217
0.8829	High Similarity	NPC37116
0.8803	High Similarity	NPC269642
0.8803	High Similarity	NPC107493
0.8793	High Similarity	NPC268530
0.8793	High Similarity	NPC154491
0.8739	High Similarity	NPC475065
0.8727	High Similarity	NPC329048
0.8727	High Similarity	NPC330011
0.8718	High Similarity	NPC4021
0.8718	High Similarity	NPC159456
0.8707	High Similarity	NPC476960
0.8707	High Similarity	NPC475520
0.8707	High Similarity	NPC475041
0.8678	High Similarity	NPC476966
0.8673	High Similarity	NPC476163
0.8673	High Similarity	NPC69291
0.8667	High Similarity	NPC156797
0.8667	High Similarity	NPC473253
0.8667	High Similarity	NPC287423
0.8649	High Similarity	NPC473482
0.8649	High Similarity	NPC475418
0.8649	High Similarity	NPC318363
0.8632	High Similarity	NPC251226
0.8632	High Similarity	NPC476961
0.8609	High Similarity	NPC470075
0.8595	High Similarity	NPC473620
0.8584	High Similarity	NPC470960
0.8571	High Similarity	NPC173905
0.8571	High Similarity	NPC120724
0.8571	High Similarity	NPC284828
0.8571	High Similarity	NPC5475
0.8571	High Similarity	NPC472216
0.8571	High Similarity	NPC204812
0.8559	High Similarity	NPC473284
0.8547	High Similarity	NPC42673
0.8534	High Similarity	NPC55296
0.8534	High Similarity	NPC469684
0.8525	High Similarity	NPC231529
0.8525	High Similarity	NPC470880
0.8509	High Similarity	NPC269530
0.85	High Similarity	NPC241456
0.85	High Similarity	NPC32868
0.8496	Intermediate Similarity	NPC473627
0.8482	Intermediate Similarity	NPC220155
0.8475	Intermediate Similarity	NPC79579
0.8475	Intermediate Similarity	NPC476962
0.8462	Intermediate Similarity	NPC473720
0.8462	Intermediate Similarity	NPC257457
0.8462	Intermediate Similarity	NPC311554
0.8462	Intermediate Similarity	NPC153440
0.8455	Intermediate Similarity	NPC475050
0.8448	Intermediate Similarity	NPC190286
0.8448	Intermediate Similarity	NPC176840
0.844	Intermediate Similarity	NPC476897
0.8435	Intermediate Similarity	NPC25909
0.843	Intermediate Similarity	NPC203702
0.843	Intermediate Similarity	NPC120994
0.8426	Intermediate Similarity	NPC316598
0.8421	Intermediate Similarity	NPC317107
0.8421	Intermediate Similarity	NPC470076
0.8417	Intermediate Similarity	NPC473979
0.8407	Intermediate Similarity	NPC87335
0.8407	Intermediate Similarity	NPC41405
0.8393	Intermediate Similarity	NPC67321
0.8393	Intermediate Similarity	NPC187435
0.839	Intermediate Similarity	NPC230513
0.839	Intermediate Similarity	NPC473203
0.839	Intermediate Similarity	NPC5292
0.8376	Intermediate Similarity	NPC473656
0.8376	Intermediate Similarity	NPC471854
0.8364	Intermediate Similarity	NPC136289
0.8362	Intermediate Similarity	NPC474181
0.8362	Intermediate Similarity	NPC238667
0.8361	Intermediate Similarity	NPC470882
0.8361	Intermediate Similarity	NPC42399
0.8361	Intermediate Similarity	NPC473265
0.8349	Intermediate Similarity	NPC476299
0.8349	Intermediate Similarity	NPC474012
0.8348	Intermediate Similarity	NPC317687
0.8347	Intermediate Similarity	NPC469790
0.8333	Intermediate Similarity	NPC472214
0.8333	Intermediate Similarity	NPC472215
0.8333	Intermediate Similarity	NPC253826
0.832	Intermediate Similarity	NPC469673
0.8319	Intermediate Similarity	NPC472218
0.8319	Intermediate Similarity	NPC474585
0.8319	Intermediate Similarity	NPC472219
0.8319	Intermediate Similarity	NPC472217
0.8319	Intermediate Similarity	NPC472825
0.8306	Intermediate Similarity	NPC220757
0.8306	Intermediate Similarity	NPC196921
0.8305	Intermediate Similarity	NPC475913
0.8305	Intermediate Similarity	NPC284707
0.8304	Intermediate Similarity	NPC266570
0.8293	Intermediate Similarity	NPC245094
0.8288	Intermediate Similarity	NPC297617
0.8288	Intermediate Similarity	NPC72151
0.8288	Intermediate Similarity	NPC112009
0.8288	Intermediate Similarity	NPC329345
0.8288	Intermediate Similarity	NPC473283
0.8288	Intermediate Similarity	NPC476237
0.8288	Intermediate Similarity	NPC475526
0.8279	Intermediate Similarity	NPC159499
0.8276	Intermediate Similarity	NPC317210
0.8276	Intermediate Similarity	NPC250109
0.8273	Intermediate Similarity	NPC476240
0.8273	Intermediate Similarity	NPC224720
0.8273	Intermediate Similarity	NPC81530
0.8273	Intermediate Similarity	NPC282524
0.8273	Intermediate Similarity	NPC476223
0.8264	Intermediate Similarity	NPC6193
0.8257	Intermediate Similarity	NPC478056
0.8257	Intermediate Similarity	NPC159763
0.8257	Intermediate Similarity	NPC278386
0.8257	Intermediate Similarity	NPC124512
0.8257	Intermediate Similarity	NPC98868
0.8254	Intermediate Similarity	NPC476823
0.8246	Intermediate Similarity	NPC474901
0.8246	Intermediate Similarity	NPC475941
0.824	Intermediate Similarity	NPC34963
0.8235	Intermediate Similarity	NPC305260
0.8235	Intermediate Similarity	NPC473636
0.8235	Intermediate Similarity	NPC470495
0.8235	Intermediate Similarity	NPC77689
0.8235	Intermediate Similarity	NPC475834
0.8235	Intermediate Similarity	NPC474179
0.8235	Intermediate Similarity	NPC270850
0.823	Intermediate Similarity	NPC301666
0.823	Intermediate Similarity	NPC475294
0.823	Intermediate Similarity	NPC144459
0.823	Intermediate Similarity	NPC255387
0.823	Intermediate Similarity	NPC131665
0.8226	Intermediate Similarity	NPC471407
0.8226	Intermediate Similarity	NPC35109
0.822	Intermediate Similarity	NPC239273
0.822	Intermediate Similarity	NPC134430
0.822	Intermediate Similarity	NPC185287
0.822	Intermediate Similarity	NPC474518
0.822	Intermediate Similarity	NPC58662
0.822	Intermediate Similarity	NPC284068
0.822	Intermediate Similarity	NPC53396
0.822	Intermediate Similarity	NPC98249
0.8214	Intermediate Similarity	NPC296950
0.8214	Intermediate Similarity	NPC146731
0.8211	Intermediate Similarity	NPC287903
0.8205	Intermediate Similarity	NPC470953
0.8198	Intermediate Similarity	NPC32577

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 NPC709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1439
0.2-0.3	3478
0.3-0.4	2620
0.4-0.5	872
0.5-0.6	255
0.6-0.7	168
0.7-0.8	120
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9907	High Similarity	NPD7115	Discovery
0.8257	Intermediate Similarity	NPD4225	Approved
0.8034	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD6881	Approved
0.7949	Intermediate Similarity	NPD6649	Approved
0.7949	Intermediate Similarity	NPD6650	Approved
0.7913	Intermediate Similarity	NPD5697	Approved
0.7869	Intermediate Similarity	NPD6319	Approved
0.7863	Intermediate Similarity	NPD7102	Approved
0.7863	Intermediate Similarity	NPD7290	Approved
0.7863	Intermediate Similarity	NPD6883	Approved
0.7826	Intermediate Similarity	NPD6675	Approved
0.7826	Intermediate Similarity	NPD6402	Approved
0.7826	Intermediate Similarity	NPD7128	Approved
0.7826	Intermediate Similarity	NPD5739	Approved
0.7798	Intermediate Similarity	NPD6399	Phase 3
0.7797	Intermediate Similarity	NPD8130	Phase 1
0.7797	Intermediate Similarity	NPD6847	Approved
0.7797	Intermediate Similarity	NPD6617	Approved
0.7797	Intermediate Similarity	NPD6869	Approved
0.7778	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6372	Approved
0.7778	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD6014	Approved
0.7778	Intermediate Similarity	NPD6013	Approved
0.7731	Intermediate Similarity	NPD6882	Approved
0.7719	Intermediate Similarity	NPD5211	Phase 2
0.7699	Intermediate Similarity	NPD7639	Approved
0.7699	Intermediate Similarity	NPD7640	Approved
0.7692	Intermediate Similarity	NPD6011	Approved
0.7692	Intermediate Similarity	NPD7320	Approved
0.7667	Intermediate Similarity	NPD4632	Approved
0.7656	Intermediate Similarity	NPD7319	Approved
0.7619	Intermediate Similarity	NPD7492	Approved
0.7611	Intermediate Similarity	NPD7638	Approved
0.7607	Intermediate Similarity	NPD5701	Approved
0.7586	Intermediate Similarity	NPD5141	Approved
0.7581	Intermediate Similarity	NPD6054	Approved
0.7578	Intermediate Similarity	NPD7736	Approved
0.7563	Intermediate Similarity	NPD4634	Approved
0.7563	Intermediate Similarity	NPD6371	Approved
0.7563	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD6616	Approved
0.7559	Intermediate Similarity	NPD7507	Approved
0.7545	Intermediate Similarity	NPD6079	Approved
0.7544	Intermediate Similarity	NPD4696	Approved
0.7544	Intermediate Similarity	NPD5285	Approved
0.7544	Intermediate Similarity	NPD5286	Approved
0.7522	Intermediate Similarity	NPD6083	Phase 2
0.7522	Intermediate Similarity	NPD6084	Phase 2
0.7522	Intermediate Similarity	NPD7902	Approved
0.7521	Intermediate Similarity	NPD6008	Approved
0.752	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD7078	Approved
0.746	Intermediate Similarity	NPD6370	Approved
0.7455	Intermediate Similarity	NPD5785	Approved
0.7414	Intermediate Similarity	NPD4633	Approved
0.7414	Intermediate Similarity	NPD5225	Approved
0.7414	Intermediate Similarity	NPD5226	Approved
0.7414	Intermediate Similarity	NPD5224	Approved
0.7411	Intermediate Similarity	NPD7748	Approved
0.7407	Intermediate Similarity	NPD3618	Phase 1
0.7402	Intermediate Similarity	NPD7604	Phase 2
0.7395	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6686	Approved
0.7387	Intermediate Similarity	NPD7515	Phase 2
0.7381	Intermediate Similarity	NPD6015	Approved
0.7381	Intermediate Similarity	NPD6016	Approved
0.7368	Intermediate Similarity	NPD4755	Approved
0.7364	Intermediate Similarity	NPD5328	Approved
0.736	Intermediate Similarity	NPD7100	Approved
0.736	Intermediate Similarity	NPD7101	Approved
0.7355	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5175	Approved
0.735	Intermediate Similarity	NPD5174	Approved
0.7345	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6009	Approved
0.7328	Intermediate Similarity	NPD5223	Approved
0.7328	Intermediate Similarity	NPD5344	Discontinued
0.7323	Intermediate Similarity	NPD5988	Approved
0.7321	Intermediate Similarity	NPD4202	Approved
0.7311	Intermediate Similarity	NPD6412	Phase 2
0.7311	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5696	Approved
0.7302	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD5222	Approved
0.7281	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5221	Approved
0.728	Intermediate Similarity	NPD7327	Approved
0.728	Intermediate Similarity	NPD7328	Approved
0.728	Intermediate Similarity	NPD6335	Approved
0.7258	Intermediate Similarity	NPD6274	Approved
0.7257	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7900	Approved
0.7248	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD8033	Approved
0.7244	Intermediate Similarity	NPD5983	Phase 2
0.7244	Intermediate Similarity	NPD8513	Phase 3
0.7241	Intermediate Similarity	NPD4700	Approved
0.7232	Intermediate Similarity	NPD8035	Phase 2
0.7232	Intermediate Similarity	NPD8034	Phase 2
0.7231	Intermediate Similarity	NPD8293	Discontinued
0.7222	Intermediate Similarity	NPD4786	Approved
0.7222	Intermediate Similarity	NPD7516	Approved
0.7217	Intermediate Similarity	NPD5173	Approved
0.72	Intermediate Similarity	NPD6317	Approved
0.7193	Intermediate Similarity	NPD4629	Approved
0.7193	Intermediate Similarity	NPD5210	Approved
0.7193	Intermediate Similarity	NPD5695	Phase 3
0.7165	Intermediate Similarity	NPD8377	Approved
0.7165	Intermediate Similarity	NPD8294	Approved
0.7156	Intermediate Similarity	NPD1694	Approved
0.7154	Intermediate Similarity	NPD6336	Discontinued
0.7154	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD6313	Approved
0.7132	Intermediate Similarity	NPD8328	Phase 3
0.713	Intermediate Similarity	NPD4697	Phase 3
0.712	Intermediate Similarity	NPD6868	Approved
0.7119	Intermediate Similarity	NPD7632	Discontinued
0.7117	Intermediate Similarity	NPD5737	Approved
0.7117	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6672	Approved
0.7109	Intermediate Similarity	NPD8517	Approved
0.7109	Intermediate Similarity	NPD8380	Approved
0.7109	Intermediate Similarity	NPD8335	Approved
0.7109	Intermediate Similarity	NPD8516	Approved
0.7109	Intermediate Similarity	NPD8379	Approved
0.7109	Intermediate Similarity	NPD8378	Approved
0.7109	Intermediate Similarity	NPD8296	Approved
0.7109	Intermediate Similarity	NPD8515	Approved
0.7109	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4730	Approved
0.7107	Intermediate Similarity	NPD4729	Approved
0.7091	Intermediate Similarity	NPD6684	Approved
0.7091	Intermediate Similarity	NPD5330	Approved
0.7091	Intermediate Similarity	NPD6409	Approved
0.7091	Intermediate Similarity	NPD7334	Approved
0.7091	Intermediate Similarity	NPD7146	Approved
0.7091	Intermediate Similarity	NPD7521	Approved
0.708	Intermediate Similarity	NPD7637	Suspended
0.708	Intermediate Similarity	NPD5693	Phase 1
0.708	Intermediate Similarity	NPD5284	Approved
0.708	Intermediate Similarity	NPD5281	Approved
0.7054	Intermediate Similarity	NPD4753	Phase 2
0.7043	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD5363	Approved
0.7	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5248	Approved
0.6992	Remote Similarity	NPD5249	Phase 3
0.6992	Remote Similarity	NPD5251	Approved
0.6992	Remote Similarity	NPD5250	Approved
0.6992	Remote Similarity	NPD5247	Approved
0.6991	Remote Similarity	NPD46	Approved
0.6991	Remote Similarity	NPD6698	Approved
0.6977	Remote Similarity	NPD6909	Approved
0.6977	Remote Similarity	NPD6908	Approved
0.6967	Remote Similarity	NPD5128	Approved
0.6964	Remote Similarity	NPD6903	Approved
0.696	Remote Similarity	NPD8133	Approved
0.6957	Remote Similarity	NPD6001	Approved
0.6949	Remote Similarity	NPD6648	Approved
0.6942	Remote Similarity	NPD4767	Approved
0.6942	Remote Similarity	NPD4768	Approved
0.6935	Remote Similarity	NPD5215	Approved
0.6935	Remote Similarity	NPD5216	Approved
0.6935	Remote Similarity	NPD5217	Approved
0.693	Remote Similarity	NPD6411	Approved
0.6917	Remote Similarity	NPD4754	Approved
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3666	Approved
0.6909	Remote Similarity	NPD3133	Approved
0.6909	Remote Similarity	NPD3665	Phase 1
0.6903	Remote Similarity	NPD6673	Approved
0.6903	Remote Similarity	NPD6080	Approved
0.6903	Remote Similarity	NPD6904	Approved
0.6885	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5779	Approved
0.687	Remote Similarity	NPD5778	Approved
0.6855	Remote Similarity	NPD5135	Approved
0.6855	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5169	Approved
0.68	Remote Similarity	NPD5127	Approved
0.68	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6033	Approved
0.6765	Remote Similarity	NPD7260	Phase 2
0.6754	Remote Similarity	NPD6101	Approved
0.6754	Remote Similarity	NPD6051	Approved
0.6754	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4221	Approved
0.6727	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD4270	Approved
0.6727	Remote Similarity	NPD4269	Approved
0.6718	Remote Similarity	NPD6921	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