NPASS Compound

Structure

CID178981 OpenBabel06191715552D 32 37 0 0 1 0 0 0 0 0999 V2000 2.4271 2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7045 2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8200 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9540 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 2.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0880 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8200 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2219 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4899 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3559 0.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0880 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4899 0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6861 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3559 1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1266 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.5933 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 2 16 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 31 1 0 0 0 0 15 1 1 1 0 0 0 16 26 1 6 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 18 28 2 0 0 0 0 19 6 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 1 0 0 0 21 25 1 1 0 0 0 22 25 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 1 0 0 0 23 32 1 0 0 0 0 24 3 1 1 0 0 0 25 27 1 6 0 0 0 26 10 1 1 0 0 0 26 31 1 0 0 0 0 26 32 1 0 0 0 0 27 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.29
Volume:	462.888
LogP:	3.59
LogD:	2.689
LogS:	-4.377
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	5.723
Fsp3:	0.889
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:	-4.811
MDCK Permeability:	2.2467431335826404e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.946
Plasma Protein Binding (PPB):	79.34398651123047%
Volume Distribution (VD):	1.253
Pgp-substrate:	4.895498752593994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.583
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.423
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.246

ADMET: Excretion

Clearance (CL):	8.814
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.638
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.513
AMES Toxicity:	0.402
Rat Oral Acute Toxicity:	0.475
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.954
Carcinogencity:	0.738
Eye Corrosion:	0.242
Eye Irritation:	0.419
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC178981

Natural Product ID:	NPC178981
*Common Name:**	Asparacosin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YWWQQPDLTAKFSH-ANLDUCOMSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-15-7-10-26(31-14-15)16(2)27(30)23(32-26)13-21-19-6-5-17-11-18(28)8-9-24(17,3)20(19)12-22(29)25(21,27)4/h11,15-16,19-23,29-30H,5-10,12-14H2,1-4H3/t15-,16-,19-,20+,21+,22-,23+,24+,25-,26-,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H](C)[C@]3([C@H](C[C@H]4[C@@H]5CCC6=CC(=O)CC[C@]6(C)[C@H]5C[C@H]([C@]34C)O)O2)O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469492
PubChem CID:	11385250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987058]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11694	Asparagus cochinchinensis	Species	Asparagaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	24100.0	nM	PMID[479189]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[479189]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[479189]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[479189]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[479189]

☑ 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 NPC178981 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	247
0.1-0.2	1450
0.2-0.3	5136
0.3-0.4	10627
0.4-0.5	10519
0.5-0.6	5873
0.6-0.7	5161
0.7-0.8	3329
0.8-0.85	304
0.85-0.9	45
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9352	High Similarity	NPC477580
0.9259	High Similarity	NPC260665
0.9083	High Similarity	NPC477944
0.8981	High Similarity	NPC163314
0.8952	High Similarity	NPC475701
0.8868	High Similarity	NPC100955
0.8868	High Similarity	NPC121566
0.8868	High Similarity	NPC474464
0.8829	High Similarity	NPC471398
0.8807	High Similarity	NPC154856
0.8807	High Similarity	NPC52241
0.8807	High Similarity	NPC101450
0.8807	High Similarity	NPC475317
0.8796	High Similarity	NPC258323
0.8785	High Similarity	NPC63023
0.8785	High Similarity	NPC474015
0.8785	High Similarity	NPC95243
0.8783	High Similarity	NPC28532
0.8729	High Similarity	NPC473888
0.8718	High Similarity	NPC174367
0.8718	High Similarity	NPC47113
0.8716	High Similarity	NPC246205
0.8692	High Similarity	NPC471111
0.8679	High Similarity	NPC22388
0.8661	High Similarity	NPC74727
0.8661	High Similarity	NPC326542
0.8654	High Similarity	NPC187159
0.8649	High Similarity	NPC210420
0.8649	High Similarity	NPC207251
0.8649	High Similarity	NPC474265
0.8649	High Similarity	NPC130427
0.8632	High Similarity	NPC473505
0.8621	High Similarity	NPC313528
0.8611	High Similarity	NPC26798
0.8609	High Similarity	NPC471406
0.8596	High Similarity	NPC475632
0.8596	High Similarity	NPC86020
0.8571	High Similarity	NPC471627
0.8571	High Similarity	NPC471173
0.8571	High Similarity	NPC194100
0.8571	High Similarity	NPC311534
0.8559	High Similarity	NPC263827
0.8559	High Similarity	NPC285410
0.8559	High Similarity	NPC250481
0.8559	High Similarity	NPC269466
0.8547	High Similarity	NPC27363
0.8545	High Similarity	NPC128133
0.8522	High Similarity	NPC161738
0.8505	High Similarity	NPC22634
0.8496	Intermediate Similarity	NPC473882
0.8496	Intermediate Similarity	NPC474557
0.8487	Intermediate Similarity	NPC305496
0.8475	Intermediate Similarity	NPC475194
0.8468	Intermediate Similarity	NPC129340
0.8468	Intermediate Similarity	NPC470065
0.8462	Intermediate Similarity	NPC475431
0.8455	Intermediate Similarity	NPC295389
0.8448	Intermediate Similarity	NPC475187
0.844	Intermediate Similarity	NPC470309
0.8435	Intermediate Similarity	NPC239293
0.8421	Intermediate Similarity	NPC49492
0.8421	Intermediate Similarity	NPC134869
0.8421	Intermediate Similarity	NPC279638
0.8421	Intermediate Similarity	NPC266728
0.8421	Intermediate Similarity	NPC152199
0.8421	Intermediate Similarity	NPC302471
0.8421	Intermediate Similarity	NPC235539
0.8417	Intermediate Similarity	NPC293623
0.8417	Intermediate Similarity	NPC69273
0.8417	Intermediate Similarity	NPC168899
0.8411	Intermediate Similarity	NPC474022
0.8407	Intermediate Similarity	NPC317210
0.8407	Intermediate Similarity	NPC102619
0.8407	Intermediate Similarity	NPC255017
0.8403	Intermediate Similarity	NPC469750
0.8403	Intermediate Similarity	NPC250556
0.8396	Intermediate Similarity	NPC275865
0.8396	Intermediate Similarity	NPC216260
0.8396	Intermediate Similarity	NPC5358
0.8393	Intermediate Similarity	NPC197231
0.8393	Intermediate Similarity	NPC471243
0.8393	Intermediate Similarity	NPC201992
0.8378	Intermediate Similarity	NPC265655
0.8378	Intermediate Similarity	NPC8431
0.8376	Intermediate Similarity	NPC476543
0.8376	Intermediate Similarity	NPC476672
0.8376	Intermediate Similarity	NPC476544
0.8376	Intermediate Similarity	NPC182900
0.8376	Intermediate Similarity	NPC249553
0.8376	Intermediate Similarity	NPC476545
0.8376	Intermediate Similarity	NPC476675
0.8365	Intermediate Similarity	NPC111015
0.8364	Intermediate Similarity	NPC226642
0.8362	Intermediate Similarity	NPC477071
0.8349	Intermediate Similarity	NPC149124
0.8349	Intermediate Similarity	NPC75531
0.8349	Intermediate Similarity	NPC471293
0.8349	Intermediate Similarity	NPC85593
0.8349	Intermediate Similarity	NPC472227
0.8349	Intermediate Similarity	NPC31430
0.8349	Intermediate Similarity	NPC472228
0.8348	Intermediate Similarity	NPC203862
0.8348	Intermediate Similarity	NPC218970
0.8347	Intermediate Similarity	NPC471407
0.8333	Intermediate Similarity	NPC69576
0.8333	Intermediate Similarity	NPC329784
0.8333	Intermediate Similarity	NPC474906
0.8333	Intermediate Similarity	NPC471633
0.8333	Intermediate Similarity	NPC165439
0.8333	Intermediate Similarity	NPC471356
0.8333	Intermediate Similarity	NPC471357
0.8333	Intermediate Similarity	NPC243354
0.8333	Intermediate Similarity	NPC117702
0.8333	Intermediate Similarity	NPC146456
0.8333	Intermediate Similarity	NPC84949
0.8333	Intermediate Similarity	NPC179412
0.8333	Intermediate Similarity	NPC469757
0.8333	Intermediate Similarity	NPC240070
0.8333	Intermediate Similarity	NPC31354
0.8333	Intermediate Similarity	NPC18547
0.8319	Intermediate Similarity	NPC289312
0.8319	Intermediate Similarity	NPC190846
0.8319	Intermediate Similarity	NPC477253
0.8319	Intermediate Similarity	NPC473255
0.8319	Intermediate Similarity	NPC277191
0.8319	Intermediate Similarity	NPC11252
0.8319	Intermediate Similarity	NPC19888
0.8319	Intermediate Similarity	NPC476674
0.8319	Intermediate Similarity	NPC471967
0.8318	Intermediate Similarity	NPC167974
0.8318	Intermediate Similarity	NPC83709
0.8305	Intermediate Similarity	NPC305771
0.8305	Intermediate Similarity	NPC15918
0.8305	Intermediate Similarity	NPC169816
0.8305	Intermediate Similarity	NPC94072
0.8305	Intermediate Similarity	NPC156789
0.8304	Intermediate Similarity	NPC474567
0.8304	Intermediate Similarity	NPC27551
0.8304	Intermediate Similarity	NPC6206
0.8304	Intermediate Similarity	NPC114961
0.8302	Intermediate Similarity	NPC177818
0.8291	Intermediate Similarity	NPC476670
0.8291	Intermediate Similarity	NPC470312
0.8288	Intermediate Similarity	NPC195708
0.8288	Intermediate Similarity	NPC473288
0.8288	Intermediate Similarity	NPC272576
0.8279	Intermediate Similarity	NPC241008
0.8279	Intermediate Similarity	NPC173347
0.8276	Intermediate Similarity	NPC297179
0.8273	Intermediate Similarity	NPC210178
0.8273	Intermediate Similarity	NPC162033
0.8269	Intermediate Similarity	NPC98193
0.8261	Intermediate Similarity	NPC310341
0.8261	Intermediate Similarity	NPC138372
0.8261	Intermediate Similarity	NPC193382
0.8261	Intermediate Similarity	NPC244127
0.8261	Intermediate Similarity	NPC199428
0.8261	Intermediate Similarity	NPC106228
0.8261	Intermediate Similarity	NPC99620
0.8261	Intermediate Similarity	NPC5311
0.8257	Intermediate Similarity	NPC140723
0.8257	Intermediate Similarity	NPC213190
0.8246	Intermediate Similarity	NPC51978
0.8246	Intermediate Similarity	NPC251309
0.8246	Intermediate Similarity	NPC962
0.8246	Intermediate Similarity	NPC52634
0.8246	Intermediate Similarity	NPC250109
0.8246	Intermediate Similarity	NPC73455
0.8246	Intermediate Similarity	NPC62696
0.8246	Intermediate Similarity	NPC200944
0.8246	Intermediate Similarity	NPC144068
0.8246	Intermediate Similarity	NPC293038
0.8235	Intermediate Similarity	NPC160084
0.8235	Intermediate Similarity	NPC41129
0.8235	Intermediate Similarity	NPC256983
0.823	Intermediate Similarity	NPC292196
0.823	Intermediate Similarity	NPC274833
0.823	Intermediate Similarity	NPC272242
0.8226	Intermediate Similarity	NPC198361
0.8224	Intermediate Similarity	NPC309493
0.822	Intermediate Similarity	NPC470921
0.822	Intermediate Similarity	NPC202051
0.822	Intermediate Similarity	NPC42675
0.8214	Intermediate Similarity	NPC40440
0.8214	Intermediate Similarity	NPC42482
0.8214	Intermediate Similarity	NPC218853
0.8214	Intermediate Similarity	NPC170221
0.8214	Intermediate Similarity	NPC477069
0.8214	Intermediate Similarity	NPC477070
0.8214	Intermediate Similarity	NPC10064
0.8214	Intermediate Similarity	NPC476835
0.8211	Intermediate Similarity	NPC471855
0.8211	Intermediate Similarity	NPC42670
0.8211	Intermediate Similarity	NPC19124
0.8205	Intermediate Similarity	NPC161065
0.8205	Intermediate Similarity	NPC475041
0.8205	Intermediate Similarity	NPC473203
0.8205	Intermediate Similarity	NPC190939
0.8205	Intermediate Similarity	NPC319570
0.8205	Intermediate Similarity	NPC197003

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 NPC178981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1746
0.2-0.3	4109
0.3-0.4	2072
0.4-0.5	518
0.5-0.6	213
0.6-0.7	131
0.7-0.8	133
0.8-0.85	9
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9057	High Similarity	NPD6412	Phase 2
0.8938	High Similarity	NPD6054	Approved
0.8938	High Similarity	NPD6059	Approved
0.8783	High Similarity	NPD6370	Approved
0.8696	High Similarity	NPD6015	Approved
0.8696	High Similarity	NPD6016	Approved
0.8632	High Similarity	NPD7492	Approved
0.8621	High Similarity	NPD5988	Approved
0.8571	High Similarity	NPD7736	Approved
0.8559	High Similarity	NPD6616	Approved
0.8487	Intermediate Similarity	NPD7078	Approved
0.8487	Intermediate Similarity	NPD8293	Discontinued
0.8403	Intermediate Similarity	NPD7507	Approved
0.8264	Intermediate Similarity	NPD6033	Approved
0.8235	Intermediate Similarity	NPD6067	Discontinued
0.8197	Intermediate Similarity	NPD7319	Approved
0.819	Intermediate Similarity	NPD6009	Approved
0.8158	Intermediate Similarity	NPD6882	Approved
0.8136	Intermediate Similarity	NPD6319	Approved
0.8125	Intermediate Similarity	NPD7320	Approved
0.812	Intermediate Similarity	NPD7327	Approved
0.812	Intermediate Similarity	NPD7328	Approved
0.8108	Intermediate Similarity	NPD6402	Approved
0.8108	Intermediate Similarity	NPD5739	Approved
0.8108	Intermediate Similarity	NPD6675	Approved
0.8108	Intermediate Similarity	NPD7128	Approved
0.8087	Intermediate Similarity	NPD4632	Approved
0.8051	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD8297	Approved
0.7983	Intermediate Similarity	NPD8294	Approved
0.7983	Intermediate Similarity	NPD8377	Approved
0.7982	Intermediate Similarity	NPD4634	Approved
0.7965	Intermediate Similarity	NPD6899	Approved
0.7965	Intermediate Similarity	NPD6881	Approved
0.7963	Intermediate Similarity	NPD4755	Approved
0.7946	Intermediate Similarity	NPD6008	Approved
0.7925	Intermediate Similarity	NPD4202	Approved
0.7917	Intermediate Similarity	NPD8033	Approved
0.7917	Intermediate Similarity	NPD8379	Approved
0.7917	Intermediate Similarity	NPD8296	Approved
0.7917	Intermediate Similarity	NPD8378	Approved
0.7917	Intermediate Similarity	NPD8335	Approved
0.7917	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD6373	Approved
0.7895	Intermediate Similarity	NPD6372	Approved
0.7876	Intermediate Similarity	NPD5701	Approved
0.7876	Intermediate Similarity	NPD5697	Approved
0.7826	Intermediate Similarity	NPD7102	Approved
0.7826	Intermediate Similarity	NPD6883	Approved
0.7826	Intermediate Similarity	NPD7290	Approved
0.7818	Intermediate Similarity	NPD5285	Approved
0.7818	Intermediate Similarity	NPD5286	Approved
0.7818	Intermediate Similarity	NPD4700	Approved
0.7818	Intermediate Similarity	NPD4696	Approved
0.7798	Intermediate Similarity	NPD6083	Phase 2
0.7798	Intermediate Similarity	NPD6084	Phase 2
0.7769	Intermediate Similarity	NPD7503	Approved
0.7759	Intermediate Similarity	NPD6617	Approved
0.7759	Intermediate Similarity	NPD6847	Approved
0.7759	Intermediate Similarity	NPD6649	Approved
0.7759	Intermediate Similarity	NPD6869	Approved
0.7759	Intermediate Similarity	NPD6650	Approved
0.7759	Intermediate Similarity	NPD8130	Phase 1
0.7739	Intermediate Similarity	NPD6012	Approved
0.7739	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6014	Approved
0.7739	Intermediate Similarity	NPD6013	Approved
0.7698	Intermediate Similarity	NPD5956	Approved
0.7679	Intermediate Similarity	NPD5211	Phase 2
0.7679	Intermediate Similarity	NPD5225	Approved
0.7679	Intermediate Similarity	NPD5226	Approved
0.7679	Intermediate Similarity	NPD5224	Approved
0.7679	Intermediate Similarity	NPD4633	Approved
0.7652	Intermediate Similarity	NPD6011	Approved
0.7652	Intermediate Similarity	NPD6686	Approved
0.7642	Intermediate Similarity	NPD5328	Approved
0.7642	Intermediate Similarity	NPD4753	Phase 2
0.7642	Intermediate Similarity	NPD7604	Phase 2
0.7642	Intermediate Similarity	NPD8328	Phase 3
0.7627	Intermediate Similarity	NPD8133	Approved
0.7623	Intermediate Similarity	NPD5983	Phase 2
0.7615	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5174	Approved
0.7611	Intermediate Similarity	NPD5175	Approved
0.7607	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5223	Approved
0.7583	Intermediate Similarity	NPD7115	Discovery
0.7568	Intermediate Similarity	NPD7638	Approved
0.7544	Intermediate Similarity	NPD5141	Approved
0.7544	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD3618	Phase 1
0.752	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7478	Intermediate Similarity	NPD4768	Approved
0.7478	Intermediate Similarity	NPD4767	Approved
0.7456	Intermediate Similarity	NPD4754	Approved
0.7455	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD6399	Phase 3
0.7411	Intermediate Similarity	NPD5696	Approved
0.7383	Intermediate Similarity	NPD6903	Approved
0.7383	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7748	Approved
0.7358	Intermediate Similarity	NPD6684	Approved
0.7358	Intermediate Similarity	NPD5330	Approved
0.7358	Intermediate Similarity	NPD7521	Approved
0.7358	Intermediate Similarity	NPD7334	Approved
0.7358	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD7146	Approved
0.7355	Intermediate Similarity	NPD6274	Approved
0.735	Intermediate Similarity	NPD5128	Approved
0.735	Intermediate Similarity	NPD4729	Approved
0.735	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD7515	Phase 2
0.7333	Intermediate Similarity	NPD4786	Approved
0.7321	Intermediate Similarity	NPD7902	Approved
0.7317	Intermediate Similarity	NPD7100	Approved
0.7317	Intermediate Similarity	NPD7101	Approved
0.7308	Intermediate Similarity	NPD4221	Approved
0.7308	Intermediate Similarity	NPD4223	Phase 3
0.7297	Intermediate Similarity	NPD4629	Approved
0.7297	Intermediate Similarity	NPD5210	Approved
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5329	Approved
0.7236	Intermediate Similarity	NPD6335	Approved
0.7232	Intermediate Similarity	NPD4697	Phase 3
0.7232	Intermediate Similarity	NPD5221	Approved
0.7232	Intermediate Similarity	NPD5222	Approved
0.7232	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5250	Approved
0.7227	Intermediate Similarity	NPD5247	Approved
0.7227	Intermediate Similarity	NPD5249	Phase 3
0.7227	Intermediate Similarity	NPD5248	Approved
0.7227	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD6001	Approved
0.72	Intermediate Similarity	NPD6909	Approved
0.72	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6908	Approved
0.717	Intermediate Similarity	NPD4197	Approved
0.7168	Intermediate Similarity	NPD5173	Approved
0.7167	Intermediate Similarity	NPD5215	Approved
0.7167	Intermediate Similarity	NPD5216	Approved
0.7167	Intermediate Similarity	NPD5217	Approved
0.7156	Intermediate Similarity	NPD6673	Approved
0.7156	Intermediate Similarity	NPD6080	Approved
0.7156	Intermediate Similarity	NPD6904	Approved
0.7154	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7107	Intermediate Similarity	NPD6053	Discontinued
0.7097	Intermediate Similarity	NPD6314	Approved
0.7097	Intermediate Similarity	NPD6313	Approved
0.7083	Intermediate Similarity	NPD5135	Approved
0.7083	Intermediate Similarity	NPD5169	Approved
0.7083	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5737	Approved
0.7064	Intermediate Similarity	NPD6672	Approved
0.7054	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7900	Approved
0.704	Intermediate Similarity	NPD4522	Approved
0.7037	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD4689	Approved
0.7037	Intermediate Similarity	NPD4138	Approved
0.7037	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4690	Approved
0.7037	Intermediate Similarity	NPD4688	Approved
0.7037	Intermediate Similarity	NPD5205	Approved
0.7027	Intermediate Similarity	NPD5281	Approved
0.7027	Intermediate Similarity	NPD8035	Phase 2
0.7027	Intermediate Similarity	NPD8034	Phase 2
0.7027	Intermediate Similarity	NPD5284	Approved
0.7025	Intermediate Similarity	NPD5127	Approved
0.6964	Remote Similarity	NPD8171	Discontinued
0.6952	Remote Similarity	NPD6928	Phase 2
0.6952	Remote Similarity	NPD7525	Registered
0.6944	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD7632	Discontinued
0.6917	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4788	Approved
0.6909	Remote Similarity	NPD5208	Approved
0.6881	Remote Similarity	NPD4694	Approved
0.6881	Remote Similarity	NPD5280	Approved
0.6881	Remote Similarity	NPD5690	Phase 2
0.6881	Remote Similarity	NPD5279	Phase 3
0.6881	Remote Similarity	NPD6098	Approved
0.6875	Remote Similarity	NPD5693	Phase 1
0.6875	Remote Similarity	NPD6050	Approved
0.6855	Remote Similarity	NPD5167	Approved
0.6818	Remote Similarity	NPD3573	Approved
0.681	Remote Similarity	NPD4225	Approved
0.68	Remote Similarity	NPD6868	Approved
0.6797	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD8513	Phase 3
0.6797	Remote Similarity	NPD8516	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