NPASS Compound

Structure

NPC469314 OpenBabel07101718272D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.0247 2.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 -2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0443 -2.3054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8110 5.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0869 5.8146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4475 -0.4029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3432 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7705 0.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4196 3.4134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0716 2.6893 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7705 1.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7207 4.3401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0687 5.0642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1157 4.8616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6738 4.5426 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3698 5.9908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1854 3.9349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 31 1 6 0 0 0 21 25 1 0 0 0 0 21 32 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 33 2 0 0 0 0 24 28 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 6 0 0 0 27 35 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.36
Volume:	587.527
LogP:	6.263
LogD:	4.491
LogS:	-6.042
# Rotatable Bonds:	9
TPSA:	91.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.16
Synthetic Accessibility Score:	5.479
Fsp3:	0.848
Lipinski Rule-of-5:	Rejected
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:	-5.122
MDCK Permeability:	1.4230297892936505e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.142
30% Bioavailability (F30%):	0.85

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	90.41905975341797%
Volume Distribution (VD):	1.762
Pgp-substrate:	4.580842971801758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	4.472
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.37
Drug-inuced Liver Injury (DILI):	0.805
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.541
Maximum Recommended Daily Dose:	0.715
Skin Sensitization:	0.053
Carcinogencity:	0.111
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC469314

Natural Product ID:	NPC469314
*Common Name:**	(8S,10S,11S,14R)-11-Hydroxy-4,4,8,10,14-Pentamethyl-17-[(2R,4S,5S)-4,5,6-Trihydroxy-6-Methylheptan-2-Yl]-1,2,5,6,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:	(8S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-17-[(2R,4S,5S)-4,5,6-trihydroxy-6-methylheptan-2-yl]-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	HNOSJVWYGXOFRP-CABDFSJESA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-17(15-21(32)25(34)27(4,5)35)18-9-13-29(7)19(18)16-20(31)24-28(6)12-11-23(33)26(2,3)22(28)10-14-30(24,29)8/h17,20-22,24-25,31-32,34-35H,9-16H2,1-8H3/t17-,20+,21+,22?,24?,25+,28+,29+,30+/m1/s1
SMILES:	O[C@H]([C@@H](C(O)(C)C)O)C[C@H](C1=C2C[C@H](O)C3[C@]([C@]2(CC1)C)(C)CCC1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL102361
PubChem CID:	44335365
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
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	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	5.8	%	PMID[495210]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	21.4	%	PMID[495210]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	30.0	%	PMID[495210]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	112.7	%	PMID[495210]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	111.2	%	PMID[495210]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	10000.0	nM	PMID[495210]

☑ 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 NPC469314 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	206
0.1-0.2	1516
0.2-0.3	5113
0.3-0.4	14640
0.4-0.5	8518
0.5-0.6	5418
0.6-0.7	5309
0.7-0.8	1821
0.8-0.85	127
0.85-0.9	10
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC241875
1.0	High Similarity	NPC469317
0.9529	High Similarity	NPC473166
0.9506	High Similarity	NPC86370
0.9419	High Similarity	NPC274046
0.9419	High Similarity	NPC198074
0.9302	High Similarity	NPC473167
0.9294	High Similarity	NPC469319
0.9294	High Similarity	NPC229871
0.9205	High Similarity	NPC37787
0.9205	High Similarity	NPC180557
0.9205	High Similarity	NPC30677
0.9205	High Similarity	NPC469329
0.9205	High Similarity	NPC473415
0.8989	High Similarity	NPC473170
0.8901	High Similarity	NPC471784
0.8901	High Similarity	NPC303777
0.8889	High Similarity	NPC471777
0.8876	High Similarity	NPC240617
0.8851	High Similarity	NPC77263
0.8851	High Similarity	NPC250592
0.8851	High Similarity	NPC32830
0.8837	High Similarity	NPC138756
0.8837	High Similarity	NPC469322
0.8721	High Similarity	NPC471737
0.8706	High Similarity	NPC473157
0.8652	High Similarity	NPC155304
0.8621	High Similarity	NPC90652
0.8617	High Similarity	NPC469316
0.8605	High Similarity	NPC197823
0.8539	High Similarity	NPC136801
0.8526	High Similarity	NPC324001
0.8523	High Similarity	NPC474677
0.8523	High Similarity	NPC470417
0.8523	High Similarity	NPC193360
0.8511	High Similarity	NPC469327
0.8511	High Similarity	NPC476897
0.8444	Intermediate Similarity	NPC235704
0.8427	Intermediate Similarity	NPC1015
0.8427	Intermediate Similarity	NPC31985
0.8427	Intermediate Similarity	NPC474245
0.8427	Intermediate Similarity	NPC122116
0.8404	Intermediate Similarity	NPC473176
0.8387	Intermediate Similarity	NPC474785
0.8387	Intermediate Similarity	NPC474938
0.837	Intermediate Similarity	NPC200702
0.8351	Intermediate Similarity	NPC470587
0.8333	Intermediate Similarity	NPC85173
0.8333	Intermediate Similarity	NPC126993
0.8315	Intermediate Similarity	NPC230387
0.8315	Intermediate Similarity	NPC44181
0.8295	Intermediate Similarity	NPC213412
0.8295	Intermediate Similarity	NPC56588
0.828	Intermediate Similarity	NPC471822
0.8276	Intermediate Similarity	NPC59453
0.8276	Intermediate Similarity	NPC221758
0.8265	Intermediate Similarity	NPC469318
0.8265	Intermediate Similarity	NPC473173
0.8265	Intermediate Similarity	NPC473165
0.8265	Intermediate Similarity	NPC471783
0.8265	Intermediate Similarity	NPC9457
0.8261	Intermediate Similarity	NPC473172
0.8256	Intermediate Similarity	NPC212083
0.8256	Intermediate Similarity	NPC151519
0.8242	Intermediate Similarity	NPC86266
0.8242	Intermediate Similarity	NPC110657
0.8242	Intermediate Similarity	NPC189520
0.8242	Intermediate Similarity	NPC212301
0.8222	Intermediate Similarity	NPC119416
0.8222	Intermediate Similarity	NPC474704
0.8222	Intermediate Similarity	NPC475921
0.8202	Intermediate Similarity	NPC475740
0.8202	Intermediate Similarity	NPC99909
0.8202	Intermediate Similarity	NPC73064
0.8191	Intermediate Similarity	NPC170978
0.8191	Intermediate Similarity	NPC9613
0.8191	Intermediate Similarity	NPC247139
0.8182	Intermediate Similarity	NPC470574
0.8182	Intermediate Similarity	NPC133954
0.8172	Intermediate Similarity	NPC32118
0.8163	Intermediate Similarity	NPC472655
0.8161	Intermediate Similarity	NPC472743
0.8161	Intermediate Similarity	NPC475726
0.8152	Intermediate Similarity	NPC474806
0.8152	Intermediate Similarity	NPC170220
0.8152	Intermediate Similarity	NPC107674
0.8152	Intermediate Similarity	NPC141497
0.8152	Intermediate Similarity	NPC275809
0.8152	Intermediate Similarity	NPC133579
0.8152	Intermediate Similarity	NPC12722
0.8144	Intermediate Similarity	NPC191892
0.8144	Intermediate Similarity	NPC471005
0.8132	Intermediate Similarity	NPC46758
0.8132	Intermediate Similarity	NPC126369
0.8132	Intermediate Similarity	NPC49320
0.8132	Intermediate Similarity	NPC111110
0.8132	Intermediate Similarity	NPC470589
0.8118	Intermediate Similarity	NPC476812
0.8111	Intermediate Similarity	NPC292491
0.8111	Intermediate Similarity	NPC310752
0.8111	Intermediate Similarity	NPC53911
0.8111	Intermediate Similarity	NPC242864
0.8111	Intermediate Similarity	NPC471722
0.8105	Intermediate Similarity	NPC191565
0.8095	Intermediate Similarity	NPC472746
0.8095	Intermediate Similarity	NPC149249
0.809	Intermediate Similarity	NPC31564
0.809	Intermediate Similarity	NPC474733
0.809	Intermediate Similarity	NPC74363
0.809	Intermediate Similarity	NPC89077
0.809	Intermediate Similarity	NPC73038
0.809	Intermediate Similarity	NPC158393
0.809	Intermediate Similarity	NPC145879
0.809	Intermediate Similarity	NPC51014
0.809	Intermediate Similarity	NPC474732
0.809	Intermediate Similarity	NPC474778
0.809	Intermediate Similarity	NPC72133
0.809	Intermediate Similarity	NPC475862
0.809	Intermediate Similarity	NPC473168
0.8085	Intermediate Similarity	NPC473158
0.8085	Intermediate Similarity	NPC73004
0.8085	Intermediate Similarity	NPC204961
0.8085	Intermediate Similarity	NPC158371
0.8085	Intermediate Similarity	NPC207922
0.8085	Intermediate Similarity	NPC259733
0.8085	Intermediate Similarity	NPC88847
0.8085	Intermediate Similarity	NPC473164
0.8085	Intermediate Similarity	NPC173744
0.8085	Intermediate Similarity	NPC117133
0.8068	Intermediate Similarity	NPC180834
0.8068	Intermediate Similarity	NPC475745
0.8068	Intermediate Similarity	NPC474482
0.8068	Intermediate Similarity	NPC171789
0.8065	Intermediate Similarity	NPC32407
0.8065	Intermediate Similarity	NPC231063
0.8065	Intermediate Similarity	NPC209662
0.8065	Intermediate Similarity	NPC263548
0.8065	Intermediate Similarity	NPC88116
0.8065	Intermediate Similarity	NPC49670
0.8065	Intermediate Similarity	NPC472977
0.8065	Intermediate Similarity	NPC114159
0.8065	Intermediate Similarity	NPC474690
0.8065	Intermediate Similarity	NPC145667
0.8065	Intermediate Similarity	NPC282395
0.8065	Intermediate Similarity	NPC6818
0.8065	Intermediate Similarity	NPC174051
0.8065	Intermediate Similarity	NPC67831
0.8065	Intermediate Similarity	NPC20235
0.8065	Intermediate Similarity	NPC196485
0.8065	Intermediate Similarity	NPC299996
0.8065	Intermediate Similarity	NPC472976
0.8065	Intermediate Similarity	NPC245972
0.8065	Intermediate Similarity	NPC191412
0.8046	Intermediate Similarity	NPC30166
0.8046	Intermediate Similarity	NPC469325
0.8046	Intermediate Similarity	NPC48362
0.8043	Intermediate Similarity	NPC235884
0.8043	Intermediate Similarity	NPC71074
0.8043	Intermediate Similarity	NPC52021
0.8043	Intermediate Similarity	NPC472149
0.8043	Intermediate Similarity	NPC262870
0.8043	Intermediate Similarity	NPC131872
0.8043	Intermediate Similarity	NPC272746
0.8043	Intermediate Similarity	NPC84319
0.8043	Intermediate Similarity	NPC300351
0.8043	Intermediate Similarity	NPC306541
0.8043	Intermediate Similarity	NPC25299
0.8023	Intermediate Similarity	NPC13554
0.8023	Intermediate Similarity	NPC22403
0.8022	Intermediate Similarity	NPC270768
0.8022	Intermediate Similarity	NPC143232
0.8022	Intermediate Similarity	NPC130520
0.8022	Intermediate Similarity	NPC274330
0.8022	Intermediate Similarity	NPC61543
0.8022	Intermediate Similarity	NPC225585
0.8022	Intermediate Similarity	NPC293048
0.8022	Intermediate Similarity	NPC220498
0.8022	Intermediate Similarity	NPC234346
0.8022	Intermediate Similarity	NPC127689
0.8022	Intermediate Similarity	NPC76879
0.8022	Intermediate Similarity	NPC198664
0.8022	Intermediate Similarity	NPC59263
0.8022	Intermediate Similarity	NPC121798
0.8022	Intermediate Similarity	NPC263393
0.8021	Intermediate Similarity	NPC110149
0.8021	Intermediate Similarity	NPC35239
0.8021	Intermediate Similarity	NPC316964
0.802	Intermediate Similarity	NPC470065
0.8	Intermediate Similarity	NPC58063
0.8	Intermediate Similarity	NPC259788
0.8	Intermediate Similarity	NPC142361
0.8	Intermediate Similarity	NPC272451
0.8	Intermediate Similarity	NPC477926
0.8	Intermediate Similarity	NPC141292
0.8	Intermediate Similarity	NPC174619
0.8	Intermediate Similarity	NPC474684
0.8	Intermediate Similarity	NPC264005
0.8	Intermediate Similarity	NPC255589
0.8	Intermediate Similarity	NPC269360
0.8	Intermediate Similarity	NPC190554

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 NPC469314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1914
0.2-0.3	3907
0.3-0.4	2166
0.4-0.5	546
0.5-0.6	169
0.6-0.7	194
0.7-0.8	68
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
0.8276	Intermediate Similarity	NPD4786	Approved
0.8256	Intermediate Similarity	NPD3667	Approved
0.809	Intermediate Similarity	NPD3618	Phase 1
0.8022	Intermediate Similarity	NPD5328	Approved
0.7849	Intermediate Similarity	NPD6079	Approved
0.7849	Intermediate Similarity	NPD7515	Phase 2
0.7816	Intermediate Similarity	NPD7525	Registered
0.7812	Intermediate Similarity	NPD4755	Approved
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD4202	Approved
0.7711	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3665	Phase 1
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.7667	Intermediate Similarity	NPD3133	Approved
0.7667	Intermediate Similarity	NPD3666	Approved
0.7653	Intermediate Similarity	NPD5285	Approved
0.7653	Intermediate Similarity	NPD4700	Approved
0.7653	Intermediate Similarity	NPD5286	Approved
0.7653	Intermediate Similarity	NPD4696	Approved
0.7634	Intermediate Similarity	NPD4753	Phase 2
0.7579	Intermediate Similarity	NPD6399	Phase 3
0.7558	Intermediate Similarity	NPD6117	Approved
0.7556	Intermediate Similarity	NPD4788	Approved
0.7526	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD4697	Phase 3
0.7526	Intermediate Similarity	NPD5221	Approved
0.7526	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7471	Intermediate Similarity	NPD6116	Phase 1
0.747	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7128	Approved
0.7451	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD5739	Approved
0.7449	Intermediate Similarity	NPD5173	Approved
0.7442	Intermediate Similarity	NPD3703	Phase 2
0.7426	Intermediate Similarity	NPD5174	Approved
0.7426	Intermediate Similarity	NPD5175	Approved
0.74	Intermediate Similarity	NPD5223	Approved
0.7386	Intermediate Similarity	NPD6115	Approved
0.7386	Intermediate Similarity	NPD3617	Approved
0.7386	Intermediate Similarity	NPD6118	Approved
0.7386	Intermediate Similarity	NPD6114	Approved
0.7386	Intermediate Similarity	NPD6697	Approved
0.7381	Intermediate Similarity	NPD4244	Approved
0.7381	Intermediate Similarity	NPD4245	Approved
0.7353	Intermediate Similarity	NPD5141	Approved
0.7349	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5360	Phase 3
0.7333	Intermediate Similarity	NPD4634	Approved
0.7326	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7303	Intermediate Similarity	NPD7645	Phase 2
0.7292	Intermediate Similarity	NPD8034	Phase 2
0.7292	Intermediate Similarity	NPD8035	Phase 2
0.7282	Intermediate Similarity	NPD4768	Approved
0.7282	Intermediate Similarity	NPD4767	Approved
0.7273	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD7902	Approved
0.7273	Intermediate Similarity	NPD6083	Phase 2
0.7262	Intermediate Similarity	NPD3698	Phase 2
0.7255	Intermediate Similarity	NPD4754	Approved
0.7253	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD4221	Approved
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7245	Intermediate Similarity	NPD5210	Approved
0.7245	Intermediate Similarity	NPD4629	Approved
0.7241	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7238	Intermediate Similarity	NPD6373	Approved
0.7238	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD5697	Approved
0.7212	Intermediate Similarity	NPD5701	Approved
0.7204	Intermediate Similarity	NPD5329	Approved
0.72	Intermediate Similarity	NPD7638	Approved
0.7196	Intermediate Similarity	NPD8297	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7159	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD4692	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD4139	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7129	Intermediate Similarity	NPD7640	Approved
0.7129	Intermediate Similarity	NPD7639	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD4197	Approved
0.7075	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6412	Phase 2
0.7037	Intermediate Similarity	NPD6882	Approved
0.7033	Intermediate Similarity	NPD4748	Discontinued
0.7033	Intermediate Similarity	NPD4695	Discontinued
0.7009	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5249	Phase 3
0.7009	Intermediate Similarity	NPD5247	Approved
0.7009	Intermediate Similarity	NPD5251	Approved
0.7009	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD3671	Phase 1
0.699	Remote Similarity	NPD7632	Discontinued
0.6988	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6011	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4632	Approved
0.697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7900	Approved
0.6947	Remote Similarity	NPD4623	Approved
0.6947	Remote Similarity	NPD4693	Phase 3
0.6947	Remote Similarity	NPD4519	Discontinued
0.6947	Remote Similarity	NPD7334	Approved
0.6947	Remote Similarity	NPD6684	Approved
0.6947	Remote Similarity	NPD4689	Approved
0.6947	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD6409	Approved
0.6947	Remote Similarity	NPD7521	Approved
0.6947	Remote Similarity	NPD5205	Approved
0.6947	Remote Similarity	NPD5330	Approved
0.6947	Remote Similarity	NPD4688	Approved
0.6947	Remote Similarity	NPD7146	Approved
0.6947	Remote Similarity	NPD4138	Approved
0.6944	Remote Similarity	NPD5216	Approved
0.6944	Remote Similarity	NPD5215	Approved
0.6944	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5217	Approved
0.6932	Remote Similarity	NPD6924	Approved
0.6932	Remote Similarity	NPD6926	Approved
0.6907	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD4758	Discontinued
0.6863	Remote Similarity	NPD5696	Approved
0.6863	Remote Similarity	NPD4225	Approved
0.6852	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5135	Approved
0.6852	Remote Similarity	NPD5169	Approved
0.6848	Remote Similarity	NPD7509	Discontinued
0.6822	Remote Similarity	NPD5168	Approved
0.6813	Remote Similarity	NPD5364	Discontinued
0.6804	Remote Similarity	NPD6672	Approved
0.6804	Remote Similarity	NPD6903	Approved
0.6804	Remote Similarity	NPD5737	Approved
0.6789	Remote Similarity	NPD5127	Approved
0.6786	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5690	Phase 2
0.6771	Remote Similarity	NPD5280	Approved
0.6771	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD6411	Approved
0.6754	Remote Similarity	NPD6059	Approved
0.6754	Remote Similarity	NPD6054	Approved
0.6754	Remote Similarity	NPD6319	Approved
0.6733	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6081	Approved
0.6701	Remote Similarity	NPD7524	Approved
0.6697	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6638	Remote Similarity	NPD6370	Approved
0.6637	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6632	Remote Similarity	NPD6695	Phase 3
0.661	Remote Similarity	NPD7507	Approved
0.6607	Remote Similarity	NPD5167	Approved
0.66	Remote Similarity	NPD5281	Approved
0.66	Remote Similarity	NPD5284	Approved
0.6598	Remote Similarity	NPD6098	Approved
0.6579	Remote Similarity	NPD6335	Approved
0.6571	Remote Similarity	NPD4159	Approved
0.6566	Remote Similarity	NPD6080	Approved
0.6566	Remote Similarity	NPD6904	Approved
0.6566	Remote Similarity	NPD6101	Approved
0.6566	Remote Similarity	NPD6673	Approved
0.6566	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7338	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data