NPASS Compound

Structure

NPC100391 OpenBabel07101718192D 35 38 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 -0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9449 2.7499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 6.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8963 0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2812 2.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 0.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2757 2.0068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8745 1.1977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4837 1.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 3.2321 4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3972 0.6219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6176 0.5286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 6 30 1 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 26 2 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 3 1 6 0 0 0 20 24 1 0 0 0 0 21 4 1 6 0 0 0 21 28 1 0 0 0 0 22 17 1 1 0 0 0 22 35 1 0 0 0 0 23 29 1 6 0 0 0 24 30 1 6 0 0 0 25 26 1 0 0 0 0 25 29 1 1 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 33 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 6 0 0 0 30 31 1 6 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.36
Volume:	535.121
LogP:	6.588
LogD:	5.375
LogS:	-6.539
# Rotatable Bonds:	8
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.281
Synthetic Accessibility Score:	5.059
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.723
MDCK Permeability:	2.9705408451263793e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.184

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	95.30062103271484%
Volume Distribution (VD):	1.577
Pgp-substrate:	2.4694936275482178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.349
CYP2C19-substrate:	0.926
CYP2C9-inhibitor:	0.617
CYP2C9-substrate:	0.118
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.378
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.678

ADMET: Excretion

Clearance (CL):	7.17
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.452
Drug-inuced Liver Injury (DILI):	0.736
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.898
Carcinogencity:	0.118
Eye Corrosion:	0.33
Eye Irritation:	0.058
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC100391

Natural Product ID:	NPC100391
*Common Name:**	Methyl (23R,25R)-3,4-Seco-9Beta-H-Lanosta-4(28),7-Dien-26,23-Olid-3-Oate
IUPAC Name:	methyl 3-[(3R,3aR,5aS,6S,7S,9bR)-3a,6,9b-trimethyl-3-[(2R)-1-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:
Standard InCHIKey:	IIPIWCJQGIFRHH-CVMHBQFTSA-N
Standard InCHI:	InChI=1S/C31H48O4/c1-19(2)23-9-10-26-25(29(23,5)14-13-27(32)34-8)12-16-30(6)24(11-15-31(26,30)7)20(3)17-22-18-21(4)28(33)35-22/h10,20-25H,1,9,11-18H2,2-8H3/t20-,21-,22-,23+,24-,25-,29+,30-,31+/m1/s1
SMILES:	COC(=O)CC[C@@]1(C)[C@@H](CC=C2[C@H]1CC[C@]1([C@@]2(C)CC[C@@H]1[C@@H](C[C@H]1OC(=O)[C@@H](C1)C)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518106
PubChem CID:	637031
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
NPO23553	Abies sachalinensis	Species	Pinaceae	Eukaryota	Barks	n.a.	n.a.	PMID[12444693]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	trunk	n.a.	n.a.	PMID[24224862]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	Trunk	n.a.	n.a.	PMID[26812172]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30063340]
NPO23553	Abies sachalinensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29383	Abies holophylla	Species	Pinaceae	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
Others	1

Activity Type	# Activity
Cell Line	6
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	75700.0	nM	PMID[533984]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	17300.0	nM	PMID[533985]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	8100.0	nM	PMID[533985]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	5500.0	nM	PMID[533985]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[533985]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	123.1	%	PMID[533985]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[533985]

☑ 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 NPC100391 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	185
0.1-0.2	1185
0.2-0.3	6358
0.3-0.4	15331
0.4-0.5	6514
0.5-0.6	6773
0.6-0.7	5103
0.7-0.8	1155
0.8-0.85	78
0.85-0.9	10
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC167877
0.9383	High Similarity	NPC470223
0.9277	High Similarity	NPC28227
0.9012	High Similarity	NPC240302
0.9	High Similarity	NPC170038
0.8875	High Similarity	NPC118987
0.8851	High Similarity	NPC470224
0.881	High Similarity	NPC264127
0.8764	High Similarity	NPC322063
0.875	High Similarity	NPC35574
0.8667	High Similarity	NPC475894
0.8621	High Similarity	NPC471896
0.8621	High Similarity	NPC111585
0.8621	High Similarity	NPC148414
0.8621	High Similarity	NPC175628
0.8605	High Similarity	NPC294480
0.8605	High Similarity	NPC226863
0.8605	High Similarity	NPC472220
0.8605	High Similarity	NPC97884
0.8588	High Similarity	NPC470051
0.8588	High Similarity	NPC195640
0.8588	High Similarity	NPC470050
0.8571	High Similarity	NPC271387
0.8571	High Similarity	NPC165064
0.8571	High Similarity	NPC153792
0.8556	High Similarity	NPC307164
0.8554	High Similarity	NPC133391
0.8539	High Similarity	NPC56525
0.8523	High Similarity	NPC150383
0.8523	High Similarity	NPC154101
0.8523	High Similarity	NPC26888
0.8506	High Similarity	NPC474889
0.8506	High Similarity	NPC474570
0.8506	High Similarity	NPC474679
0.85	High Similarity	NPC41017
0.8488	Intermediate Similarity	NPC312215
0.8471	Intermediate Similarity	NPC323765
0.8444	Intermediate Similarity	NPC469599
0.8434	Intermediate Similarity	NPC475665
0.8434	Intermediate Similarity	NPC327002
0.8434	Intermediate Similarity	NPC232625
0.8415	Intermediate Similarity	NPC44083
0.8415	Intermediate Similarity	NPC477371
0.8415	Intermediate Similarity	NPC327674
0.8415	Intermediate Similarity	NPC153987
0.8391	Intermediate Similarity	NPC183546
0.8391	Intermediate Similarity	NPC474845
0.8391	Intermediate Similarity	NPC477128
0.8372	Intermediate Similarity	NPC212843
0.8372	Intermediate Similarity	NPC155011
0.837	Intermediate Similarity	NPC252295
0.8353	Intermediate Similarity	NPC469407
0.8353	Intermediate Similarity	NPC109512
0.8333	Intermediate Similarity	NPC472223
0.8333	Intermediate Similarity	NPC159410
0.8333	Intermediate Similarity	NPC327969
0.8333	Intermediate Similarity	NPC472224
0.8333	Intermediate Similarity	NPC321289
0.8315	Intermediate Similarity	NPC218301
0.8315	Intermediate Similarity	NPC297265
0.8313	Intermediate Similarity	NPC195424
0.8295	Intermediate Similarity	NPC475921
0.8295	Intermediate Similarity	NPC54689
0.8295	Intermediate Similarity	NPC474704
0.8293	Intermediate Similarity	NPC321514
0.8293	Intermediate Similarity	NPC4827
0.828	Intermediate Similarity	NPC476303
0.828	Intermediate Similarity	NPC470906
0.8276	Intermediate Similarity	NPC233836
0.8276	Intermediate Similarity	NPC187376
0.8276	Intermediate Similarity	NPC474684
0.8276	Intermediate Similarity	NPC142361
0.8276	Intermediate Similarity	NPC96496
0.8276	Intermediate Similarity	NPC159046
0.8261	Intermediate Similarity	NPC292133
0.8256	Intermediate Similarity	NPC329738
0.8242	Intermediate Similarity	NPC69548
0.8242	Intermediate Similarity	NPC184848
0.8235	Intermediate Similarity	NPC470047
0.8235	Intermediate Similarity	NPC470046
0.8235	Intermediate Similarity	NPC477373
0.8235	Intermediate Similarity	NPC470948
0.8222	Intermediate Similarity	NPC475657
0.8222	Intermediate Similarity	NPC470375
0.8222	Intermediate Similarity	NPC152897
0.8222	Intermediate Similarity	NPC141497
0.8222	Intermediate Similarity	NPC107674
0.8222	Intermediate Similarity	NPC66429
0.8222	Intermediate Similarity	NPC470376
0.8222	Intermediate Similarity	NPC170220
0.8214	Intermediate Similarity	NPC147066
0.8214	Intermediate Similarity	NPC201912
0.8214	Intermediate Similarity	NPC38350
0.8214	Intermediate Similarity	NPC474955
0.8214	Intermediate Similarity	NPC477372
0.8211	Intermediate Similarity	NPC36321
0.8211	Intermediate Similarity	NPC140723
0.8202	Intermediate Similarity	NPC220454
0.8202	Intermediate Similarity	NPC212679
0.8202	Intermediate Similarity	NPC474842
0.8202	Intermediate Similarity	NPC44240
0.8202	Intermediate Similarity	NPC469595
0.8202	Intermediate Similarity	NPC123854
0.8202	Intermediate Similarity	NPC475965
0.8202	Intermediate Similarity	NPC46281
0.8182	Intermediate Similarity	NPC242864
0.8182	Intermediate Similarity	NPC250687
0.8182	Intermediate Similarity	NPC247406
0.8182	Intermediate Similarity	NPC254572
0.8182	Intermediate Similarity	NPC229407
0.8182	Intermediate Similarity	NPC48824
0.8182	Intermediate Similarity	NPC48866
0.8172	Intermediate Similarity	NPC477813
0.8161	Intermediate Similarity	NPC6979
0.8161	Intermediate Similarity	NPC28252
0.8161	Intermediate Similarity	NPC55309
0.8152	Intermediate Similarity	NPC58052
0.8152	Intermediate Similarity	NPC111684
0.814	Intermediate Similarity	NPC139566
0.814	Intermediate Similarity	NPC320801
0.8132	Intermediate Similarity	NPC471720
0.8132	Intermediate Similarity	NPC294266
0.8125	Intermediate Similarity	NPC228669
0.8125	Intermediate Similarity	NPC471293
0.8125	Intermediate Similarity	NPC164835
0.8125	Intermediate Similarity	NPC255309
0.8125	Intermediate Similarity	NPC472227
0.8125	Intermediate Similarity	NPC472228
0.8118	Intermediate Similarity	NPC178676
0.8118	Intermediate Similarity	NPC100297
0.8118	Intermediate Similarity	NPC296367
0.8118	Intermediate Similarity	NPC260956
0.8111	Intermediate Similarity	NPC212301
0.8111	Intermediate Similarity	NPC110657
0.8111	Intermediate Similarity	NPC189520
0.8111	Intermediate Similarity	NPC190442
0.8111	Intermediate Similarity	NPC23434
0.8111	Intermediate Similarity	NPC86266
0.809	Intermediate Similarity	NPC476733
0.809	Intermediate Similarity	NPC155479
0.809	Intermediate Similarity	NPC473039
0.809	Intermediate Similarity	NPC84271
0.809	Intermediate Similarity	NPC305039
0.809	Intermediate Similarity	NPC269267
0.809	Intermediate Similarity	NPC215029
0.809	Intermediate Similarity	NPC77168
0.809	Intermediate Similarity	NPC288699
0.809	Intermediate Similarity	NPC102414
0.8085	Intermediate Similarity	NPC239768
0.8085	Intermediate Similarity	NPC476274
0.8085	Intermediate Similarity	NPC128698
0.8068	Intermediate Similarity	NPC38885
0.8068	Intermediate Similarity	NPC162107
0.8068	Intermediate Similarity	NPC46912
0.8068	Intermediate Similarity	NPC128644
0.8065	Intermediate Similarity	NPC107243
0.8065	Intermediate Similarity	NPC57416
0.8065	Intermediate Similarity	NPC23680
0.8049	Intermediate Similarity	NPC92489
0.8049	Intermediate Similarity	NPC899
0.8046	Intermediate Similarity	NPC189311
0.8046	Intermediate Similarity	NPC283733
0.8046	Intermediate Similarity	NPC52628
0.8046	Intermediate Similarity	NPC470048
0.8046	Intermediate Similarity	NPC98270
0.8046	Intermediate Similarity	NPC474218
0.8043	Intermediate Similarity	NPC222845
0.8043	Intermediate Similarity	NPC33473
0.8043	Intermediate Similarity	NPC279974
0.8043	Intermediate Similarity	NPC45324
0.8043	Intermediate Similarity	NPC263347
0.8043	Intermediate Similarity	NPC162001
0.8041	Intermediate Similarity	NPC96377
0.8025	Intermediate Similarity	NPC166797
0.8025	Intermediate Similarity	NPC306928
0.8023	Intermediate Similarity	NPC83569
0.8023	Intermediate Similarity	NPC469561
0.8023	Intermediate Similarity	NPC471037
0.8023	Intermediate Similarity	NPC170862
0.8023	Intermediate Similarity	NPC167103
0.8023	Intermediate Similarity	NPC69279
0.8023	Intermediate Similarity	NPC22611
0.8023	Intermediate Similarity	NPC271784
0.8022	Intermediate Similarity	NPC474436
0.8022	Intermediate Similarity	NPC63118
0.8022	Intermediate Similarity	NPC474185
0.8022	Intermediate Similarity	NPC229976
0.8022	Intermediate Similarity	NPC243866
0.8022	Intermediate Similarity	NPC49776
0.8021	Intermediate Similarity	NPC176883
0.8021	Intermediate Similarity	NPC476237
0.8021	Intermediate Similarity	NPC36688
0.8	Intermediate Similarity	NPC224720
0.8	Intermediate Similarity	NPC469400
0.8	Intermediate Similarity	NPC476223
0.8	Intermediate Similarity	NPC477149
0.8	Intermediate Similarity	NPC476988
0.8	Intermediate Similarity	NPC476240
0.8	Intermediate Similarity	NPC474327
0.8	Intermediate Similarity	NPC477147

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 NPC100391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1529
0.2-0.3	4286
0.3-0.4	2153
0.4-0.5	549
0.5-0.6	184
0.6-0.7	223
0.7-0.8	53
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD6399	Phase 3
0.8605	High Similarity	NPD6672	Approved
0.8605	High Similarity	NPD5737	Approved
0.8605	High Similarity	NPD6903	Approved
0.8588	High Similarity	NPD7334	Approved
0.8588	High Similarity	NPD6409	Approved
0.8588	High Similarity	NPD7146	Approved
0.8588	High Similarity	NPD6684	Approved
0.8588	High Similarity	NPD7521	Approved
0.8588	High Similarity	NPD5330	Approved
0.8444	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD5207	Approved
0.8161	Intermediate Similarity	NPD6098	Approved
0.809	Intermediate Similarity	NPD6080	Approved
0.809	Intermediate Similarity	NPD6673	Approved
0.809	Intermediate Similarity	NPD6904	Approved
0.7935	Intermediate Similarity	NPD6001	Approved
0.7931	Intermediate Similarity	NPD4786	Approved
0.7912	Intermediate Similarity	NPD6050	Approved
0.7872	Intermediate Similarity	NPD6084	Phase 2
0.7872	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD6008	Approved
0.7849	Intermediate Similarity	NPD5695	Phase 3
0.7802	Intermediate Similarity	NPD5692	Phase 3
0.7789	Intermediate Similarity	NPD5696	Approved
0.7778	Intermediate Similarity	NPD5208	Approved
0.7742	Intermediate Similarity	NPD7900	Approved
0.7742	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3668	Phase 3
0.7717	Intermediate Similarity	NPD5693	Phase 1
0.7717	Intermediate Similarity	NPD8034	Phase 2
0.7717	Intermediate Similarity	NPD8035	Phase 2
0.7717	Intermediate Similarity	NPD5694	Approved
0.7701	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD3667	Approved
0.7692	Intermediate Similarity	NPD6051	Approved
0.7653	Intermediate Similarity	NPD6052	Approved
0.764	Intermediate Similarity	NPD1694	Approved
0.7556	Intermediate Similarity	NPD3618	Phase 1
0.7553	Intermediate Similarity	NPD7748	Approved
0.7528	Intermediate Similarity	NPD3666	Approved
0.7528	Intermediate Similarity	NPD3665	Phase 1
0.7528	Intermediate Similarity	NPD3133	Approved
0.7527	Intermediate Similarity	NPD5281	Approved
0.7527	Intermediate Similarity	NPD5284	Approved
0.7525	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7451	Intermediate Similarity	NPD6373	Approved
0.7451	Intermediate Similarity	NPD6372	Approved
0.7444	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5279	Phase 3
0.7353	Intermediate Similarity	NPD6881	Approved
0.7353	Intermediate Similarity	NPD6899	Approved
0.734	Intermediate Similarity	NPD6079	Approved
0.734	Intermediate Similarity	NPD7515	Phase 2
0.7312	Intermediate Similarity	NPD4753	Phase 2
0.7308	Intermediate Similarity	NPD6650	Approved
0.7308	Intermediate Similarity	NPD6649	Approved
0.7303	Intermediate Similarity	NPD4221	Approved
0.7303	Intermediate Similarity	NPD4223	Phase 3
0.7292	Intermediate Similarity	NPD5654	Approved
0.7255	Intermediate Similarity	NPD5701	Approved
0.7255	Intermediate Similarity	NPD5697	Approved
0.7253	Intermediate Similarity	NPD5329	Approved
0.7245	Intermediate Similarity	NPD7638	Approved
0.7241	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4747	Approved
0.7222	Intermediate Similarity	NPD5362	Discontinued
0.7216	Intermediate Similarity	NPD4697	Phase 3
0.7212	Intermediate Similarity	NPD7102	Approved
0.7212	Intermediate Similarity	NPD7290	Approved
0.7212	Intermediate Similarity	NPD6883	Approved
0.7184	Intermediate Similarity	NPD6011	Approved
0.7176	Intermediate Similarity	NPD5733	Approved
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD5777	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD5959	Approved
0.7115	Intermediate Similarity	NPD6013	Approved
0.7115	Intermediate Similarity	NPD6014	Approved
0.7115	Intermediate Similarity	NPD6012	Approved
0.7113	Intermediate Similarity	NPD4629	Approved
0.7113	Intermediate Similarity	NPD5210	Approved
0.7108	Intermediate Similarity	NPD4137	Phase 3
0.7097	Intermediate Similarity	NPD3573	Approved
0.7093	Intermediate Similarity	NPD7339	Approved
0.7093	Intermediate Similarity	NPD6942	Approved
0.7093	Intermediate Similarity	NPD8039	Approved
0.7087	Intermediate Similarity	NPD6614	Approved
0.7083	Intermediate Similarity	NPD4202	Approved
0.7075	Intermediate Similarity	NPD8297	Approved
0.7075	Intermediate Similarity	NPD6882	Approved
0.7041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5222	Approved
0.7041	Intermediate Similarity	NPD5221	Approved
0.7041	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4691	Approved
0.7	Intermediate Similarity	NPD5369	Approved
0.6989	Remote Similarity	NPD5280	Approved
0.6989	Remote Similarity	NPD4688	Approved
0.6989	Remote Similarity	NPD5205	Approved
0.6989	Remote Similarity	NPD4693	Phase 3
0.6989	Remote Similarity	NPD4689	Approved
0.6989	Remote Similarity	NPD4138	Approved
0.6989	Remote Similarity	NPD4690	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4694	Approved
0.6989	Remote Similarity	NPD5690	Phase 2
0.6988	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7637	Suspended
0.6977	Remote Similarity	NPD4687	Approved
0.6972	Remote Similarity	NPD7115	Discovery
0.697	Remote Similarity	NPD5173	Approved
0.697	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD6101	Approved
0.6947	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5276	Approved
0.6923	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD6435	Approved
0.6889	Remote Similarity	NPD7525	Registered
0.6882	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6868	Approved
0.6875	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3617	Approved
0.6848	Remote Similarity	NPD4788	Approved
0.6832	Remote Similarity	NPD4696	Approved
0.6832	Remote Similarity	NPD5286	Approved
0.6832	Remote Similarity	NPD4700	Approved
0.6832	Remote Similarity	NPD5285	Approved
0.6818	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6117	Approved
0.6813	Remote Similarity	NPD4139	Approved
0.6813	Remote Similarity	NPD4692	Approved
0.6782	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6926	Approved
0.6782	Remote Similarity	NPD6924	Approved
0.6782	Remote Similarity	NPD4058	Approved
0.6771	Remote Similarity	NPD1695	Approved
0.6771	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5223	Approved
0.6759	Remote Similarity	NPD6053	Discontinued
0.6757	Remote Similarity	NPD6335	Approved
0.6744	Remote Similarity	NPD4243	Approved
0.6742	Remote Similarity	NPD6116	Phase 1
0.6739	Remote Similarity	NPD4270	Approved
0.6739	Remote Similarity	NPD4269	Approved
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6733	Remote Similarity	NPD4225	Approved
0.6727	Remote Similarity	NPD6274	Approved
0.6705	Remote Similarity	NPD3702	Approved
0.6703	Remote Similarity	NPD5368	Approved
0.6703	Remote Similarity	NPD4695	Discontinued
0.6701	Remote Similarity	NPD5785	Approved
0.67	Remote Similarity	NPD7732	Phase 3
0.6699	Remote Similarity	NPD5225	Approved
0.6699	Remote Similarity	NPD5224	Approved
0.6699	Remote Similarity	NPD5226	Approved
0.6699	Remote Similarity	NPD5211	Phase 2
0.6699	Remote Similarity	NPD4633	Approved
0.6697	Remote Similarity	NPD7094	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6697	Remote Similarity	NPD6858	Approved
0.6696	Remote Similarity	NPD7492	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6638	Remote Similarity	NPD6616	Approved
0.6637	Remote Similarity	NPD6059	Approved
0.6637	Remote Similarity	NPD6054	Approved
0.6635	Remote Similarity	NPD5174	Approved
0.6635	Remote Similarity	NPD5175	Approved
0.6635	Remote Similarity	NPD4754	Approved
0.6632	Remote Similarity	NPD5786	Approved
0.663	Remote Similarity	NPD4790	Discontinued
0.6629	Remote Similarity	NPD6933	Approved
0.6609	Remote Similarity	NPD7122	Discontinued
0.6607	Remote Similarity	NPD6313	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