NPASS Compound

Structure

NPC470587 OpenBabel07101718312D 37 41 0 0 1 0 0 0 0 0999 V2000 4.0377 -0.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5927 5.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5927 5.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0354 3.5154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2267 2.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4947 4.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 4.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0898 2.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9588 3.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6776 2.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0927 2.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4947 1.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3904 0.1339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4644 1.5462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3686 0.3418 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6776 1.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4947 3.1019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6286 1.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 1.6019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2267 4.1019 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.9588 4.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2565 2.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3607 2.6019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.0927 4.6019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6286 2.6019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2267 3.1019 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7213 0.8770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2267 1.1019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8248 4.6019 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9997 3.1935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3055 2.8333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0522 1.6202 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 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 24 1 0 0 0 0 16 31 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 19 25 1 0 0 0 0 19 29 1 1 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 32 1 1 0 0 0 22 27 1 0 0 0 0 22 30 1 0 0 0 0 23 27 1 0 0 0 0 23 33 2 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 30 1 6 0 0 0 26 28 1 0 0 0 0 26 31 1 0 0 0 0 26 37 1 0 0 0 0 28 37 1 0 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 31 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.35
Volume:	546.782
LogP:	3.963
LogD:	2.742
LogS:	-4.492
# Rotatable Bonds:	6
TPSA:	107.36
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.372
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.486
MDCK Permeability:	1.3218217645771801e-05
Pgp-inhibitor:	0.724
Pgp-substrate:	0.39
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.151
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	91.5517807006836%
Volume Distribution (VD):	0.607
Pgp-substrate:	4.106081962585449%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.35
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	6.17
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.155
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.042
Carcinogencity:	0.44
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC470587

Natural Product ID:	NPC470587
*Common Name:**	Alisol B 23-Acetate
IUPAC Name:	(3S,5R)-3-(3,3-dimethyloxiran-2-yl)-3-hydroxy-5-[(8S,9R,10S,11S,14R)-11-hydroxy-4,4,10,14-tetramethyl-3-oxo-2,5,6,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]hexanoic acid
Synonyms:
Standard InCHIKey:	CPYFCYMXHGAZTF-WXYIYAPGSA-N
Standard InCHI:	InChI=1S/C31H48O6/c1-17(15-31(36,16-24(34)35)26-28(4,5)37-26)18-10-12-29(6)19-8-9-22-27(2,3)23(33)11-13-30(22,7)25(19)21(32)14-20(18)29/h17,19,21-22,25-26,32,36H,8-16H2,1-7H3,(H,34,35)/t17-,19+,21+,22?,25+,26?,29-,30+,31+/m1/s1
SMILES:	OC(=O)C[C@](C1OC1(C)C)(C[C@H](C1=C2C[C@H](O)[C@@H]3[C@@H]([C@]2(CC1)C)CCC1[C@]3(C)CCC(=O)C1(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2074634
PubChem CID:	70695224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	3

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	36180.0	nM	PMID[549838]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	600.0	nM	PMID[549836]
NPT610	Others	Molecular identity unknown		PPB	=	80.6	%	PMID[549837]
NPT610	Others	Molecular identity unknown		PPB	=	82.19	%	PMID[549837]
NPT610	Others	Molecular identity unknown		PPB	=	78.2	%	PMID[549837]

☑ 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 NPC470587 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	264
0.1-0.2	1761
0.2-0.3	5146
0.3-0.4	9427
0.4-0.5	11648
0.5-0.6	6585
0.6-0.7	5146
0.7-0.8	2580
0.8-0.85	116
0.85-0.9	17
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9118	High Similarity	NPC473165
0.9	High Similarity	NPC469327
0.898	High Similarity	NPC471777
0.8878	High Similarity	NPC469329
0.8878	High Similarity	NPC180557
0.8878	High Similarity	NPC473415
0.8878	High Similarity	NPC30677
0.8878	High Similarity	NPC37787
0.8866	High Similarity	NPC274046
0.8866	High Similarity	NPC198074
0.8835	High Similarity	NPC472655
0.8788	High Similarity	NPC471822
0.8776	High Similarity	NPC240617
0.875	High Similarity	NPC471783
0.875	High Similarity	NPC9457
0.8725	High Similarity	NPC469316
0.8649	High Similarity	NPC154491
0.8649	High Similarity	NPC251226
0.8649	High Similarity	NPC268530
0.8571	High Similarity	NPC4021
0.8571	High Similarity	NPC473166
0.8571	High Similarity	NPC159456
0.8559	High Similarity	NPC42673
0.8532	High Similarity	NPC284915
0.8485	Intermediate Similarity	NPC469315
0.8411	Intermediate Similarity	NPC218853
0.8396	Intermediate Similarity	NPC469318
0.8396	Intermediate Similarity	NPC473173
0.8381	Intermediate Similarity	NPC475036
0.8381	Intermediate Similarity	NPC471293
0.8381	Intermediate Similarity	NPC65523
0.8378	Intermediate Similarity	NPC55296
0.8351	Intermediate Similarity	NPC469314
0.8351	Intermediate Similarity	NPC469322
0.8351	Intermediate Similarity	NPC241875
0.8351	Intermediate Similarity	NPC469317
0.8349	Intermediate Similarity	NPC152117
0.8349	Intermediate Similarity	NPC234042
0.8349	Intermediate Similarity	NPC476163
0.8348	Intermediate Similarity	NPC469790
0.8333	Intermediate Similarity	NPC250956
0.8333	Intermediate Similarity	NPC470065
0.8333	Intermediate Similarity	NPC5284
0.8318	Intermediate Similarity	NPC273155
0.8318	Intermediate Similarity	NPC469845
0.8286	Intermediate Similarity	NPC277074
0.8286	Intermediate Similarity	NPC324001
0.8286	Intermediate Similarity	NPC471005
0.8286	Intermediate Similarity	NPC264048
0.8286	Intermediate Similarity	NPC209298
0.8276	Intermediate Similarity	NPC120994
0.8276	Intermediate Similarity	NPC203702
0.8273	Intermediate Similarity	NPC255017
0.8261	Intermediate Similarity	NPC469789
0.8257	Intermediate Similarity	NPC474229
0.8241	Intermediate Similarity	NPC41405
0.8235	Intermediate Similarity	NPC256227
0.823	Intermediate Similarity	NPC230513
0.8224	Intermediate Similarity	NPC112780
0.8224	Intermediate Similarity	NPC166993
0.8224	Intermediate Similarity	NPC59530
0.8214	Intermediate Similarity	NPC58662
0.8198	Intermediate Similarity	NPC117712
0.8182	Intermediate Similarity	NPC269530
0.8173	Intermediate Similarity	NPC477655
0.8155	Intermediate Similarity	NPC170978
0.8155	Intermediate Similarity	NPC190080
0.8155	Intermediate Similarity	NPC111187
0.8148	Intermediate Similarity	NPC231278
0.8148	Intermediate Similarity	NPC94942
0.8148	Intermediate Similarity	NPC112895
0.8148	Intermediate Similarity	NPC218123
0.8131	Intermediate Similarity	NPC200957
0.8131	Intermediate Similarity	NPC138908
0.8131	Intermediate Similarity	NPC181357
0.8131	Intermediate Similarity	NPC102352
0.8125	Intermediate Similarity	NPC207217
0.8125	Intermediate Similarity	NPC298278
0.8125	Intermediate Similarity	NPC173686
0.8125	Intermediate Similarity	NPC16081
0.8125	Intermediate Similarity	NPC270929
0.812	Intermediate Similarity	NPC293112
0.8113	Intermediate Similarity	NPC122811
0.8113	Intermediate Similarity	NPC87927
0.8113	Intermediate Similarity	NPC218513
0.8113	Intermediate Similarity	NPC55954
0.8113	Intermediate Similarity	NPC312900
0.8108	Intermediate Similarity	NPC477266
0.8103	Intermediate Similarity	NPC11895
0.8095	Intermediate Similarity	NPC163963
0.8095	Intermediate Similarity	NPC46848
0.8095	Intermediate Similarity	NPC476897
0.8095	Intermediate Similarity	NPC52899
0.8095	Intermediate Similarity	NPC289148
0.8091	Intermediate Similarity	NPC472003
0.8091	Intermediate Similarity	NPC469656
0.8091	Intermediate Similarity	NPC474846
0.8091	Intermediate Similarity	NPC469655
0.8087	Intermediate Similarity	NPC67569
0.8087	Intermediate Similarity	NPC102822
0.8087	Intermediate Similarity	NPC477046
0.8077	Intermediate Similarity	NPC470067
0.8077	Intermediate Similarity	NPC303777
0.8077	Intermediate Similarity	NPC471784
0.8077	Intermediate Similarity	NPC470066
0.8077	Intermediate Similarity	NPC471038
0.8077	Intermediate Similarity	NPC470068
0.8077	Intermediate Similarity	NPC475876
0.8073	Intermediate Similarity	NPC87335
0.8073	Intermediate Similarity	NPC154906
0.807	Intermediate Similarity	NPC473203
0.807	Intermediate Similarity	NPC61520
0.807	Intermediate Similarity	NPC258592
0.807	Intermediate Similarity	NPC178548
0.807	Intermediate Similarity	NPC161065
0.8056	Intermediate Similarity	NPC144854
0.8056	Intermediate Similarity	NPC3316
0.8056	Intermediate Similarity	NPC230541
0.8053	Intermediate Similarity	NPC287343
0.8053	Intermediate Similarity	NPC97908
0.8053	Intermediate Similarity	NPC122033
0.8053	Intermediate Similarity	NPC183580
0.8053	Intermediate Similarity	NPC474654
0.8053	Intermediate Similarity	NPC470493
0.8053	Intermediate Similarity	NPC470854
0.8053	Intermediate Similarity	NPC312824
0.8051	Intermediate Similarity	NPC298841
0.8037	Intermediate Similarity	NPC96268
0.8037	Intermediate Similarity	NPC284865
0.8037	Intermediate Similarity	NPC301787
0.8036	Intermediate Similarity	NPC323821
0.8036	Intermediate Similarity	NPC472274
0.8036	Intermediate Similarity	NPC45218
0.8036	Intermediate Similarity	NPC243354
0.8036	Intermediate Similarity	NPC268238
0.8036	Intermediate Similarity	NPC143268
0.8034	Intermediate Similarity	NPC8369
0.8034	Intermediate Similarity	NPC81736
0.8034	Intermediate Similarity	NPC172154
0.802	Intermediate Similarity	NPC235704
0.8019	Intermediate Similarity	NPC148628
0.8019	Intermediate Similarity	NPC471119
0.8019	Intermediate Similarity	NPC275990
0.8019	Intermediate Similarity	NPC88203
0.8019	Intermediate Similarity	NPC296879
0.8019	Intermediate Similarity	NPC286519
0.8019	Intermediate Similarity	NPC477054
0.8019	Intermediate Similarity	NPC246736
0.8019	Intermediate Similarity	NPC193934
0.8019	Intermediate Similarity	NPC76866
0.8019	Intermediate Similarity	NPC304832
0.8019	Intermediate Similarity	NPC214946
0.8019	Intermediate Similarity	NPC271980
0.8018	Intermediate Similarity	NPC280782
0.8018	Intermediate Similarity	NPC472002
0.8018	Intermediate Similarity	NPC476964
0.8017	Intermediate Similarity	NPC170538
0.8017	Intermediate Similarity	NPC23786
0.8017	Intermediate Similarity	NPC470265
0.8017	Intermediate Similarity	NPC65858
0.8	Intermediate Similarity	NPC100908
0.8	Intermediate Similarity	NPC477656
0.8	Intermediate Similarity	NPC475463
0.8	Intermediate Similarity	NPC287676
0.8	Intermediate Similarity	NPC77001
0.8	Intermediate Similarity	NPC94906
0.8	Intermediate Similarity	NPC167974
0.8	Intermediate Similarity	NPC35239
0.8	Intermediate Similarity	NPC470388
0.8	Intermediate Similarity	NPC471093
0.8	Intermediate Similarity	NPC253618
0.8	Intermediate Similarity	NPC241192
0.7982	Intermediate Similarity	NPC153587
0.7982	Intermediate Similarity	NPC709
0.7982	Intermediate Similarity	NPC469916
0.7982	Intermediate Similarity	NPC17772
0.7982	Intermediate Similarity	NPC211224
0.7982	Intermediate Similarity	NPC113448
0.7982	Intermediate Similarity	NPC297179
0.7982	Intermediate Similarity	NPC186525
0.7982	Intermediate Similarity	NPC154608
0.7982	Intermediate Similarity	NPC329736
0.7982	Intermediate Similarity	NPC472439
0.7982	Intermediate Similarity	NPC63841
0.7982	Intermediate Similarity	NPC192813
0.7982	Intermediate Similarity	NPC277017
0.7982	Intermediate Similarity	NPC50774
0.7981	Intermediate Similarity	NPC253586
0.7981	Intermediate Similarity	NPC272451
0.7966	Intermediate Similarity	NPC473635
0.7965	Intermediate Similarity	NPC96312
0.7965	Intermediate Similarity	NPC40632
0.7965	Intermediate Similarity	NPC302471
0.7965	Intermediate Similarity	NPC251236
0.7965	Intermediate Similarity	NPC328374
0.7965	Intermediate Similarity	NPC179626
0.7963	Intermediate Similarity	NPC222833
0.7963	Intermediate Similarity	NPC37600
0.7963	Intermediate Similarity	NPC278628
0.7963	Intermediate Similarity	NPC475494

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 NPC470587 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	2134
0.2-0.3	3762
0.3-0.4	1919
0.4-0.5	618
0.5-0.6	264
0.6-0.7	184
0.7-0.8	33
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD7115	Discovery
0.7895	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6319	Approved
0.7636	Intermediate Similarity	NPD6402	Approved
0.7636	Intermediate Similarity	NPD5739	Approved
0.7636	Intermediate Similarity	NPD6008	Approved
0.7636	Intermediate Similarity	NPD7128	Approved
0.7636	Intermediate Similarity	NPD6675	Approved
0.7596	Intermediate Similarity	NPD6399	Phase 3
0.7589	Intermediate Similarity	NPD6373	Approved
0.7589	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6372	Approved
0.7544	Intermediate Similarity	NPD8297	Approved
0.7522	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.7478	Intermediate Similarity	NPD4632	Approved
0.7456	Intermediate Similarity	NPD6650	Approved
0.7456	Intermediate Similarity	NPD6649	Approved
0.7438	Intermediate Similarity	NPD7492	Approved
0.7411	Intermediate Similarity	NPD5701	Approved
0.7411	Intermediate Similarity	NPD5697	Approved
0.7398	Intermediate Similarity	NPD7736	Approved
0.7395	Intermediate Similarity	NPD6054	Approved
0.7395	Intermediate Similarity	NPD6059	Approved
0.7377	Intermediate Similarity	NPD6616	Approved
0.7368	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD7290	Approved
0.7368	Intermediate Similarity	NPD6883	Approved
0.7368	Intermediate Similarity	NPD7102	Approved
0.7339	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD8035	Phase 2
0.7333	Intermediate Similarity	NPD8034	Phase 2
0.7317	Intermediate Similarity	NPD7078	Approved
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7315	Intermediate Similarity	NPD7902	Approved
0.7304	Intermediate Similarity	NPD6869	Approved
0.7304	Intermediate Similarity	NPD6847	Approved
0.7304	Intermediate Similarity	NPD8130	Phase 1
0.7304	Intermediate Similarity	NPD6617	Approved
0.7281	Intermediate Similarity	NPD6014	Approved
0.7281	Intermediate Similarity	NPD6012	Approved
0.7281	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD6370	Approved
0.7257	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7638	Approved
0.7248	Intermediate Similarity	NPD4225	Approved
0.7241	Intermediate Similarity	NPD6882	Approved
0.7236	Intermediate Similarity	NPD7507	Approved
0.7213	Intermediate Similarity	NPD7604	Phase 2
0.7196	Intermediate Similarity	NPD7748	Approved
0.7193	Intermediate Similarity	NPD6011	Approved
0.719	Intermediate Similarity	NPD6016	Approved
0.719	Intermediate Similarity	NPD6015	Approved
0.7182	Intermediate Similarity	NPD7640	Approved
0.7182	Intermediate Similarity	NPD7639	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.717	Intermediate Similarity	NPD6411	Approved
0.7156	Intermediate Similarity	NPD4755	Approved
0.7155	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7131	Intermediate Similarity	NPD5988	Approved
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6118	Approved
0.7071	Intermediate Similarity	NPD6114	Approved
0.7071	Intermediate Similarity	NPD6697	Approved
0.7071	Intermediate Similarity	NPD6115	Approved
0.7054	Intermediate Similarity	NPD7632	Discontinued
0.7049	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD6921	Approved
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5285	Approved
0.7027	Intermediate Similarity	NPD4700	Approved
0.7027	Intermediate Similarity	NPD5286	Approved
0.7027	Intermediate Similarity	NPD4696	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.699	Remote Similarity	NPD4786	Approved
0.6981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6101	Approved
0.697	Remote Similarity	NPD6116	Phase 1
0.6961	Remote Similarity	NPD3667	Approved
0.696	Remote Similarity	NPD6336	Discontinued
0.6944	Remote Similarity	NPD5778	Approved
0.6944	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD3703	Phase 2
0.6923	Remote Similarity	NPD6371	Approved
0.6917	Remote Similarity	NPD6274	Approved
0.6909	Remote Similarity	NPD4697	Phase 3
0.6903	Remote Similarity	NPD5225	Approved
0.6903	Remote Similarity	NPD4633	Approved
0.6903	Remote Similarity	NPD5211	Phase 2
0.6903	Remote Similarity	NPD5224	Approved
0.6903	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD6686	Approved
0.6891	Remote Similarity	NPD8133	Approved
0.6885	Remote Similarity	NPD7101	Approved
0.6885	Remote Similarity	NPD7100	Approved
0.6869	Remote Similarity	NPD6117	Approved
0.6857	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6033	Approved
0.6842	Remote Similarity	NPD5174	Approved
0.6842	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5223	Approved
0.6814	Remote Similarity	NPD1700	Approved
0.6803	Remote Similarity	NPD6335	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD5696	Approved
0.6783	Remote Similarity	NPD5141	Approved
0.6774	Remote Similarity	NPD6908	Approved
0.6774	Remote Similarity	NPD8513	Phase 3
0.6774	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD8517	Approved
0.6774	Remote Similarity	NPD6909	Approved
0.6774	Remote Similarity	NPD8515	Approved
0.6765	Remote Similarity	NPD7525	Registered
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5222	Approved
0.6757	Remote Similarity	NPD5221	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD4768	Approved
0.6721	Remote Similarity	NPD6317	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6697	Remote Similarity	NPD7637	Suspended
0.6697	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6696	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7328	Approved
0.664	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3573	Approved
0.6613	Remote Similarity	NPD7516	Approved
0.661	Remote Similarity	NPD5128	Approved
0.661	Remote Similarity	NPD4730	Approved
0.661	Remote Similarity	NPD4729	Approved
0.6606	Remote Similarity	NPD6698	Approved
0.6606	Remote Similarity	NPD46	Approved
0.6577	Remote Similarity	NPD5282	Discontinued
0.6574	Remote Similarity	NPD6672	Approved
0.6574	Remote Similarity	NPD5737	Approved
0.6574	Remote Similarity	NPD6903	Approved
0.656	Remote Similarity	NPD8377	Approved
0.656	Remote Similarity	NPD8294	Approved
0.6538	Remote Similarity	NPD5369	Approved
0.6529	Remote Similarity	NPD6053	Discontinued
0.6525	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5344	Discontinued
0.6514	Remote Similarity	NPD4753	Phase 2
0.6512	Remote Similarity	NPD8074	Phase 3
0.6509	Remote Similarity	NPD3665	Phase 1
0.6509	Remote Similarity	NPD3668	Phase 3
0.6509	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD3666	Approved
0.6508	Remote Similarity	NPD8296	Approved
0.6508	Remote Similarity	NPD8378	Approved
0.6508	Remote Similarity	NPD8380	Approved
0.6508	Remote Similarity	NPD8335	Approved
0.6508	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD5251	Approved
0.65	Remote Similarity	NPD5247	Approved
0.65	Remote Similarity	NPD5250	Approved
0.65	Remote Similarity	NPD5249	Phase 3
0.65	Remote Similarity	NPD5248	Approved
0.6481	Remote Similarity	NPD7524	Approved
0.6476	Remote Similarity	NPD6435	Approved
0.6465	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5216	Approved
0.6446	Remote Similarity	NPD5217	Approved
0.6446	Remote Similarity	NPD5215	Approved
0.6429	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4788	Approved
0.6406	Remote Similarity	NPD6067	Discontinued
0.6396	Remote Similarity	NPD5281	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