NPASS Compound

Structure

CID8374 OpenBabel06191715332D 35 41 0 0 1 0 0 0 0 0999 V2000 -8.8551 1.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7742 -0.7118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3555 -1.4098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8008 -0.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5846 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3390 0.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7985 -0.6791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8716 -0.5812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3816 0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5554 2.0331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3633 0.2148 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8472 -0.6139 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2824 -1.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9525 1.1413 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 -2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9038 1.0760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7420 -2.3690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3068 -1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5263 1.9310 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 12 1 0 0 0 0 2 13 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 3 1 6 0 0 0 15 10 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 26 1 1 0 0 0 17 25 1 1 0 0 0 18 26 1 0 0 0 0 18 29 2 0 0 0 0 19 28 1 1 0 0 0 19 30 1 0 0 0 0 20 28 1 1 0 0 0 20 35 1 0 0 0 0 21 27 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 14 1 6 0 0 0 23 33 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 27 1 6 0 0 0 26 28 1 1 0 0 0 27 14 1 1 0 0 0 27 34 1 0 0 0 0 28 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.25
Volume:	483.935
LogP:	3.31
LogD:	1.525
LogS:	-4.375
# Rotatable Bonds:	2
TPSA:	102.57
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	6.275
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.267
MDCK Permeability:	4.3803429434774444e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.758

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981
Plasma Protein Binding (PPB):	53.24240493774414%
Volume Distribution (VD):	1.111
Pgp-substrate:	35.8072395324707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.739
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	18.058
Half-life (T1/2):	0.553

ADMET: Toxicity

hERG Blockers:	0.516
Human Hepatotoxicity (H-HT):	0.675
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.392
Skin Sensitization:	0.573
Carcinogencity:	0.559
Eye Corrosion:	0.598
Eye Irritation:	0.155
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC8374

Natural Product ID:	NPC8374
*Common Name:**	23-Hydroxytubocapsanolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZTDAKBMARSMGBP-FVMAOMGMSA-N
Standard InCHI:	InChI=1S/C28H36O7/c1-12-13(2)24(32)33-23(22(12)31)14(3)27-21(34-27)11-17-15-10-20-28(35-20)19(30)7-6-18(29)26(28,5)16(15)8-9-25(17,27)4/h6-7,14-17,19-23,30-31H,8-11H2,1-5H3/t14-,15-,16+,17+,19+,20-,21-,22+,23+,25+,26+,27-,28-/m1/s1
SMILES:	O=C1O[C@H]([C@H](C(=C1C)C)O)[C@H]([C@@]12O[C@@H]1C[C@@H]1[C@]2(C)CC[C@H]2[C@H]1C[C@@H]1[C@]3([C@]2(C)C(=O)C=C[C@@H]3O)O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389413
PubChem CID:	16680371
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
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO28641	Tubocapsicum anomalum	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	6

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.44	ug.mL-1	PMID[465995]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.05	ug.mL-1	PMID[465995]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.79	ug.mL-1	PMID[465995]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1.19	ug.mL-1	PMID[465995]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	0.9	ug.mL-1	PMID[465995]
NPT27	Others	Unspecified		IC50	=	0.49	ug.mL-1	PMID[465995]

☑ 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 NPC8374 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	266
0.1-0.2	1452
0.2-0.3	4161
0.3-0.4	7719
0.4-0.5	13022
0.5-0.6	7068
0.6-0.7	6514
0.7-0.8	2231
0.8-0.85	161
0.85-0.9	64
0.9-0.95	35
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9825	High Similarity	NPC88326
0.9825	High Similarity	NPC153700
0.9649	High Similarity	NPC474370
0.9565	High Similarity	NPC67569
0.9561	High Similarity	NPC264954
0.9483	High Similarity	NPC23786
0.9483	High Similarity	NPC470265
0.9474	High Similarity	NPC709
0.9474	High Similarity	NPC50774
0.9402	High Similarity	NPC469789
0.9386	High Similarity	NPC470492
0.9386	High Similarity	NPC286528
0.9386	High Similarity	NPC20302
0.9386	High Similarity	NPC140055
0.9386	High Similarity	NPC167606
0.9244	High Similarity	NPC293112
0.9217	High Similarity	NPC470493
0.9217	High Similarity	NPC312824
0.9217	High Similarity	NPC183580
0.916	High Similarity	NPC172154
0.916	High Similarity	NPC81736
0.916	High Similarity	NPC8369
0.9138	High Similarity	NPC186525
0.9123	High Similarity	NPC122056
0.9076	High Similarity	NPC11895
0.9068	High Similarity	NPC46570
0.9068	High Similarity	NPC473256
0.9068	High Similarity	NPC470878
0.906	High Similarity	NPC61520
0.9043	High Similarity	NPC67259
0.9043	High Similarity	NPC147912
0.9016	High Similarity	NPC473593
0.8992	High Similarity	NPC107493
0.8992	High Similarity	NPC269642
0.8992	High Similarity	NPC170538
0.8974	High Similarity	NPC329736
0.8926	High Similarity	NPC473635
0.8898	High Similarity	NPC473274
0.8898	High Similarity	NPC475041
0.8871	High Similarity	NPC231240
0.887	High Similarity	NPC191620
0.8852	High Similarity	NPC287423
0.8852	High Similarity	NPC473253
0.8843	High Similarity	NPC470494
0.8843	High Similarity	NPC3381
0.8843	High Similarity	NPC469790
0.8803	High Similarity	NPC64318
0.8803	High Similarity	NPC270929
0.88	High Similarity	NPC316915
0.876	High Similarity	NPC204812
0.8739	High Similarity	NPC473270
0.8729	High Similarity	NPC243065
0.871	High Similarity	NPC470880
0.871	High Similarity	NPC231529
0.8707	High Similarity	NPC236217
0.8689	High Similarity	NPC241456
0.8689	High Similarity	NPC32868
0.8667	High Similarity	NPC79579
0.8667	High Similarity	NPC154491
0.8667	High Similarity	NPC268530
0.8655	High Similarity	NPC153440
0.8651	High Similarity	NPC469673
0.8644	High Similarity	NPC190286
0.864	High Similarity	NPC196921
0.864	High Similarity	NPC220757
0.8621	High Similarity	NPC474315
0.8621	High Similarity	NPC470961
0.8607	High Similarity	NPC473979
0.8595	High Similarity	NPC4021
0.8595	High Similarity	NPC159456
0.8583	High Similarity	NPC475520
0.8583	High Similarity	NPC473203
0.8583	High Similarity	NPC5292
0.8583	High Similarity	NPC476960
0.8583	High Similarity	NPC476823
0.8571	High Similarity	NPC34963
0.856	High Similarity	NPC35109
0.856	High Similarity	NPC476966
0.8559	High Similarity	NPC284915
0.8548	High Similarity	NPC473265
0.8548	High Similarity	NPC470882
0.8547	High Similarity	NPC476163
0.8534	High Similarity	NPC29133
0.8522	High Similarity	NPC472825
0.8512	High Similarity	NPC251226
0.8512	High Similarity	NPC474585
0.8512	High Similarity	NPC476961
0.8504	High Similarity	NPC58029
0.8492	Intermediate Similarity	NPC279478
0.8492	Intermediate Similarity	NPC241935
0.8487	Intermediate Similarity	NPC176840
0.8487	Intermediate Similarity	NPC470075
0.848	Intermediate Similarity	NPC473620
0.8475	Intermediate Similarity	NPC250109
0.8475	Intermediate Similarity	NPC317210
0.8455	Intermediate Similarity	NPC120724
0.8448	Intermediate Similarity	NPC284828
0.8448	Intermediate Similarity	NPC472216
0.8448	Intermediate Similarity	NPC173905
0.8448	Intermediate Similarity	NPC5475
0.8435	Intermediate Similarity	NPC91034
0.843	Intermediate Similarity	NPC305260
0.843	Intermediate Similarity	NPC42673
0.843	Intermediate Similarity	NPC270850
0.8417	Intermediate Similarity	NPC58662
0.8417	Intermediate Similarity	NPC469684
0.8417	Intermediate Similarity	NPC476965
0.8417	Intermediate Similarity	NPC239273
0.8417	Intermediate Similarity	NPC470959
0.8417	Intermediate Similarity	NPC55296
0.8413	Intermediate Similarity	NPC471407
0.84	Intermediate Similarity	NPC305496
0.839	Intermediate Similarity	NPC269530
0.8376	Intermediate Similarity	NPC37116
0.8361	Intermediate Similarity	NPC476962
0.8347	Intermediate Similarity	NPC473720
0.8347	Intermediate Similarity	NPC257457
0.8347	Intermediate Similarity	NPC311554
0.8347	Intermediate Similarity	NPC475372
0.8346	Intermediate Similarity	NPC173347
0.8333	Intermediate Similarity	NPC148458
0.8333	Intermediate Similarity	NPC311534
0.832	Intermediate Similarity	NPC120994
0.832	Intermediate Similarity	NPC15095
0.832	Intermediate Similarity	NPC159499
0.832	Intermediate Similarity	NPC203702
0.8319	Intermediate Similarity	NPC962
0.8319	Intermediate Similarity	NPC25909
0.8306	Intermediate Similarity	NPC6193
0.8305	Intermediate Similarity	NPC470076
0.8305	Intermediate Similarity	NPC317107
0.8293	Intermediate Similarity	NPC310511
0.8291	Intermediate Similarity	NPC87335
0.8291	Intermediate Similarity	NPC475065
0.8281	Intermediate Similarity	NPC476193
0.8281	Intermediate Similarity	NPC471855
0.8279	Intermediate Similarity	NPC230513
0.8279	Intermediate Similarity	NPC312536
0.8279	Intermediate Similarity	NPC278681
0.8276	Intermediate Similarity	NPC67321
0.8276	Intermediate Similarity	NPC471601
0.8276	Intermediate Similarity	NPC329048
0.8276	Intermediate Similarity	NPC187435
0.8276	Intermediate Similarity	NPC330011
0.8268	Intermediate Similarity	NPC221414
0.8264	Intermediate Similarity	NPC471854
0.8264	Intermediate Similarity	NPC185287
0.8264	Intermediate Similarity	NPC473656
0.8254	Intermediate Similarity	NPC42399
0.8254	Intermediate Similarity	NPC156797
0.825	Intermediate Similarity	NPC474181
0.825	Intermediate Similarity	NPC238667
0.825	Intermediate Similarity	NPC216665
0.824	Intermediate Similarity	NPC473255
0.8235	Intermediate Similarity	NPC207251
0.8235	Intermediate Similarity	NPC69291
0.8235	Intermediate Similarity	NPC317687
0.8235	Intermediate Similarity	NPC42658
0.822	Intermediate Similarity	NPC472214
0.822	Intermediate Similarity	NPC76084
0.822	Intermediate Similarity	NPC472215
0.8211	Intermediate Similarity	NPC112936
0.8205	Intermediate Similarity	NPC475418
0.8205	Intermediate Similarity	NPC472218
0.8205	Intermediate Similarity	NPC472219
0.8205	Intermediate Similarity	NPC318363
0.8205	Intermediate Similarity	NPC472217
0.8205	Intermediate Similarity	NPC473482
0.8197	Intermediate Similarity	NPC475913
0.8197	Intermediate Similarity	NPC146786
0.8197	Intermediate Similarity	NPC16701
0.8197	Intermediate Similarity	NPC284707
0.8197	Intermediate Similarity	NPC113448
0.8189	Intermediate Similarity	NPC473888
0.8189	Intermediate Similarity	NPC245094
0.8182	Intermediate Similarity	NPC113425
0.8182	Intermediate Similarity	NPC232564
0.8182	Intermediate Similarity	NPC49492
0.8182	Intermediate Similarity	NPC268213
0.8182	Intermediate Similarity	NPC266728
0.8154	Intermediate Similarity	NPC478072
0.8151	Intermediate Similarity	NPC470960
0.8145	Intermediate Similarity	NPC470418
0.8145	Intermediate Similarity	NPC312481
0.8136	Intermediate Similarity	NPC475941
0.8136	Intermediate Similarity	NPC474901
0.813	Intermediate Similarity	NPC35171
0.813	Intermediate Similarity	NPC473636
0.813	Intermediate Similarity	NPC472667
0.813	Intermediate Similarity	NPC213761
0.813	Intermediate Similarity	NPC474179
0.813	Intermediate Similarity	NPC77689
0.813	Intermediate Similarity	NPC475834
0.8125	Intermediate Similarity	NPC104382
0.812	Intermediate Similarity	NPC83744
0.812	Intermediate Similarity	NPC144459
0.812	Intermediate Similarity	NPC475060
0.812	Intermediate Similarity	NPC473284
0.812	Intermediate Similarity	NPC64844
0.812	Intermediate Similarity	NPC42847

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 NPC8374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	1592
0.2-0.3	3680
0.3-0.4	2391
0.4-0.5	733
0.5-0.6	264
0.6-0.7	164
0.7-0.8	89
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9386	High Similarity	NPD7115	Discovery
0.8065	Intermediate Similarity	NPD6319	Approved
0.7983	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD8297	Approved
0.7899	Intermediate Similarity	NPD6881	Approved
0.7899	Intermediate Similarity	NPD6899	Approved
0.7869	Intermediate Similarity	NPD4632	Approved
0.7851	Intermediate Similarity	NPD6649	Approved
0.7851	Intermediate Similarity	NPD6650	Approved
0.7846	Intermediate Similarity	NPD7319	Approved
0.7826	Intermediate Similarity	NPD4225	Approved
0.7815	Intermediate Similarity	NPD5697	Approved
0.7812	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD6054	Approved
0.7769	Intermediate Similarity	NPD7736	Approved
0.7769	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD6883	Approved
0.7769	Intermediate Similarity	NPD4634	Approved
0.7769	Intermediate Similarity	NPD6371	Approved
0.7769	Intermediate Similarity	NPD7102	Approved
0.7769	Intermediate Similarity	NPD7290	Approved
0.7759	Intermediate Similarity	NPD7640	Approved
0.7759	Intermediate Similarity	NPD7639	Approved
0.7752	Intermediate Similarity	NPD7507	Approved
0.7752	Intermediate Similarity	NPD6616	Approved
0.7731	Intermediate Similarity	NPD6675	Approved
0.7731	Intermediate Similarity	NPD7128	Approved
0.7731	Intermediate Similarity	NPD6402	Approved
0.7731	Intermediate Similarity	NPD5739	Approved
0.7731	Intermediate Similarity	NPD6008	Approved
0.7717	Intermediate Similarity	NPD7503	Approved
0.7705	Intermediate Similarity	NPD8130	Phase 1
0.7705	Intermediate Similarity	NPD6847	Approved
0.7705	Intermediate Similarity	NPD6617	Approved
0.7705	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD7078	Approved
0.7686	Intermediate Similarity	NPD6373	Approved
0.7686	Intermediate Similarity	NPD6014	Approved
0.7686	Intermediate Similarity	NPD6012	Approved
0.7686	Intermediate Similarity	NPD6013	Approved
0.7686	Intermediate Similarity	NPD6372	Approved
0.7672	Intermediate Similarity	NPD7638	Approved
0.7656	Intermediate Similarity	NPD6370	Approved
0.7642	Intermediate Similarity	NPD6882	Approved
0.7627	Intermediate Similarity	NPD5211	Phase 2
0.7603	Intermediate Similarity	NPD6011	Approved
0.7603	Intermediate Similarity	NPD7320	Approved
0.7597	Intermediate Similarity	NPD7604	Phase 2
0.7578	Intermediate Similarity	NPD6015	Approved
0.7578	Intermediate Similarity	NPD6016	Approved
0.7542	Intermediate Similarity	NPD5344	Discontinued
0.754	Intermediate Similarity	NPD6009	Approved
0.7521	Intermediate Similarity	NPD5701	Approved
0.7521	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.748	Intermediate Similarity	NPD7327	Approved
0.748	Intermediate Similarity	NPD7328	Approved
0.7458	Intermediate Similarity	NPD5285	Approved
0.7458	Intermediate Similarity	NPD5286	Approved
0.7458	Intermediate Similarity	NPD4696	Approved
0.7442	Intermediate Similarity	NPD8033	Approved
0.7442	Intermediate Similarity	NPD5983	Phase 2
0.7436	Intermediate Similarity	NPD6084	Phase 2
0.7436	Intermediate Similarity	NPD6083	Phase 2
0.7424	Intermediate Similarity	NPD8293	Discontinued
0.7422	Intermediate Similarity	NPD7516	Approved
0.7391	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD5785	Approved
0.7364	Intermediate Similarity	NPD8294	Approved
0.7364	Intermediate Similarity	NPD8377	Approved
0.736	Intermediate Similarity	NPD6053	Discontinued
0.7348	Intermediate Similarity	NPD6336	Discontinued
0.7333	Intermediate Similarity	NPD5226	Approved
0.7333	Intermediate Similarity	NPD5225	Approved
0.7333	Intermediate Similarity	NPD5224	Approved
0.7333	Intermediate Similarity	NPD4633	Approved
0.7317	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6686	Approved
0.7308	Intermediate Similarity	NPD8378	Approved
0.7308	Intermediate Similarity	NPD8380	Approved
0.7308	Intermediate Similarity	NPD8335	Approved
0.7308	Intermediate Similarity	NPD8379	Approved
0.7308	Intermediate Similarity	NPD8296	Approved
0.7288	Intermediate Similarity	NPD4755	Approved
0.7287	Intermediate Similarity	NPD7101	Approved
0.7287	Intermediate Similarity	NPD7100	Approved
0.728	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5175	Approved
0.7273	Intermediate Similarity	NPD5174	Approved
0.7265	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5223	Approved
0.7241	Intermediate Similarity	NPD4202	Approved
0.7227	Intermediate Similarity	NPD5696	Approved
0.7209	Intermediate Similarity	NPD6335	Approved
0.719	Intermediate Similarity	NPD7632	Discontinued
0.7188	Intermediate Similarity	NPD6274	Approved
0.7176	Intermediate Similarity	NPD8513	Phase 3
0.7167	Intermediate Similarity	NPD6648	Approved
0.7167	Intermediate Similarity	NPD4700	Approved
0.7155	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7132	Intermediate Similarity	NPD6317	Approved
0.7119	Intermediate Similarity	NPD5210	Approved
0.7119	Intermediate Similarity	NPD4629	Approved
0.7119	Intermediate Similarity	NPD5695	Phase 3
0.7097	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6314	Approved
0.7077	Intermediate Similarity	NPD6313	Approved
0.7068	Intermediate Similarity	NPD8328	Phase 3
0.7045	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8517	Approved
0.7045	Intermediate Similarity	NPD8515	Approved
0.7045	Intermediate Similarity	NPD8516	Approved
0.7043	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4730	Approved
0.704	Intermediate Similarity	NPD4729	Approved
0.7034	Intermediate Similarity	NPD6001	Approved
0.7034	Intermediate Similarity	NPD7748	Approved
0.7031	Intermediate Similarity	NPD8133	Approved
0.7018	Intermediate Similarity	NPD7521	Approved
0.7018	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6409	Approved
0.7018	Intermediate Similarity	NPD7334	Approved
0.7018	Intermediate Similarity	NPD3618	Phase 1
0.7018	Intermediate Similarity	NPD6684	Approved
0.7018	Intermediate Similarity	NPD5330	Approved
0.7018	Intermediate Similarity	NPD7146	Approved
0.7009	Intermediate Similarity	NPD5281	Approved
0.7009	Intermediate Similarity	NPD5284	Approved
0.7009	Intermediate Similarity	NPD5693	Phase 1
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD7637	Suspended
0.6985	Remote Similarity	NPD6033	Approved
0.6983	Remote Similarity	NPD4753	Phase 2
0.6983	Remote Similarity	NPD5328	Approved
0.693	Remote Similarity	NPD5363	Approved
0.6929	Remote Similarity	NPD5248	Approved
0.6929	Remote Similarity	NPD5247	Approved
0.6929	Remote Similarity	NPD5249	Phase 3
0.6929	Remote Similarity	NPD5250	Approved
0.6929	Remote Similarity	NPD5251	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6917	Remote Similarity	NPD5221	Approved
0.6917	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD5222	Approved
0.6917	Remote Similarity	NPD6908	Approved
0.6905	Remote Similarity	NPD5128	Approved
0.6897	Remote Similarity	NPD6903	Approved
0.6894	Remote Similarity	NPD4522	Approved
0.6891	Remote Similarity	NPD7900	Approved
0.6891	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4768	Approved
0.688	Remote Similarity	NPD4767	Approved
0.6875	Remote Similarity	NPD5217	Approved
0.6875	Remote Similarity	NPD5216	Approved
0.6875	Remote Similarity	NPD5215	Approved
0.6864	Remote Similarity	NPD8034	Phase 2
0.6864	Remote Similarity	NPD8035	Phase 2
0.686	Remote Similarity	NPD5173	Approved
0.6855	Remote Similarity	NPD4754	Approved
0.685	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3133	Approved
0.6842	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD3666	Approved
0.6842	Remote Similarity	NPD3665	Phase 1
0.6838	Remote Similarity	NPD6673	Approved
0.6838	Remote Similarity	NPD6904	Approved
0.6838	Remote Similarity	NPD6080	Approved
0.6807	Remote Similarity	NPD5778	Approved
0.6807	Remote Similarity	NPD5779	Approved
0.6797	Remote Similarity	NPD5135	Approved
0.6797	Remote Similarity	NPD5169	Approved
0.6797	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6868	Approved
0.6783	Remote Similarity	NPD1694	Approved
0.6777	Remote Similarity	NPD4697	Phase 3
0.6763	Remote Similarity	NPD5956	Approved
0.6752	Remote Similarity	NPD6672	Approved
0.6752	Remote Similarity	NPD5737	Approved
0.6744	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5127	Approved
0.6742	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7260	Phase 2
0.6695	Remote Similarity	NPD6051	Approved
0.6694	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD3573	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