NPASS Compound

Structure

NPC156377 OpenBabel07101718282D 39 45 0 0 1 0 0 0 0 0999 V2000 1.5600 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9281 2.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2941 -3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2941 -3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2020 -0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2074 -0.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7367 -1.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7367 1.7658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0620 -2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1960 -1.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6601 -0.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7941 -0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0223 2.1793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0620 0.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9281 0.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9722 2.0748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0620 2.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6101 1.3703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9281 -1.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1960 -0.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6601 -1.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1960 1.3522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3789 1.1613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7006 0.5090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3789 -0.4568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7941 -2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6142 0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3300 -0.1478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3300 0.8522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9281 -0.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0620 -0.1478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7912 0.3522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0620 3.8522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5261 -2.1478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0699 -1.4078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4232 0.6901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1960 2.3522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2034 0.4568 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 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 30 1 0 0 0 0 13 16 1 0 0 0 0 14 22 1 0 0 0 0 15 30 1 0 0 0 0 15 31 1 0 0 0 0 16 1 1 1 0 0 0 16 23 1 0 0 0 0 17 33 2 0 0 0 0 17 37 1 0 0 0 0 18 13 1 1 0 0 0 18 24 1 0 0 0 0 18 38 1 0 0 0 0 19 26 1 0 0 0 0 19 30 1 6 0 0 0 20 28 1 1 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 34 1 6 0 0 0 22 29 1 6 0 0 0 22 37 1 0 0 0 0 23 29 1 6 0 0 0 23 32 1 0 0 0 0 24 27 1 6 0 0 0 24 39 1 0 0 0 0 25 28 1 1 0 0 0 25 32 1 0 0 0 0 25 35 1 0 0 0 0 27 36 1 0 0 0 0 28 29 1 1 0 0 0 29 8 1 6 0 0 0 30 31 1 1 0 0 0 31 14 1 1 0 0 0 32 38 1 6 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.36
Volume:	561.028
LogP:	3.918
LogD:	3.509
LogS:	-3.977
# Rotatable Bonds:	3
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	7.182
Fsp3:	0.969
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:	-5.342
MDCK Permeability:	5.8398574765305966e-05
Pgp-inhibitor:	0.689
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.763

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	86.23004913330078%
Volume Distribution (VD):	1.124
Pgp-substrate:	8.592412948608398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	2.68
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.365
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.712
Carcinogencity:	0.014
Eye Corrosion:	0.009
Eye Irritation:	0.043
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC156377

Natural Product ID:	NPC156377
*Common Name:**	IMRBGIHKULBERF-QSPGDUCTSA-N
IUPAC Name:	n.a.
Synonyms:	12Beta-Acetoxycimigenol
Standard InCHIKey:	IMRBGIHKULBERF-QSPGDUCTSA-N
Standard InCHI:	InChI=1S/C32H50O7/c1-16-13-18-24(27(5,6)36)39-32(38-18)23(16)29(8)22(37-17(2)33)14-31-15-30(31)12-11-21(34)26(3,4)19(30)9-10-20(31)28(29,7)25(32)35/h16,18-25,34-36H,9-15H2,1-8H3/t16-,18-,19+,20+,21+,22-,23-,24+,25-,28-,29-,30-,31+,32+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@H](C(C)(C)O)O[C@]3([C@H]1[C@@]1(C)[C@@H](C[C@]45C[C@]65CC[C@@H](C(C)(C)[C@@H]6CC[C@H]4[C@]1(C)[C@H]3O)O)OC(=O)C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375361
PubChem CID:	16104912
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26366	Actaea pachypoda	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[17253859]
NPO26366	Actaea pachypoda	Species	Ranunculaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	187000.0	nM	PMID[458823]

☑ 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 NPC156377 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	499
0.1-0.2	4390
0.2-0.3	13063
0.3-0.4	10845
0.4-0.5	5559
0.5-0.6	4247
0.6-0.7	2840
0.7-0.8	972
0.8-0.85	209
0.85-0.9	48
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9468	High Similarity	NPC114700
0.9468	High Similarity	NPC310138
0.9468	High Similarity	NPC470029
0.9468	High Similarity	NPC134967
0.9462	High Similarity	NPC470030
0.9362	High Similarity	NPC472081
0.9362	High Similarity	NPC108227
0.9362	High Similarity	NPC476512
0.9333	High Similarity	NPC473066
0.9326	High Similarity	NPC228059
0.9239	High Similarity	NPC473067
0.9239	High Similarity	NPC473064
0.9239	High Similarity	NPC473065
0.9167	High Similarity	NPC476837
0.9167	High Similarity	NPC139181
0.9167	High Similarity	NPC97260
0.9158	High Similarity	NPC476839
0.9158	High Similarity	NPC476838
0.913	High Similarity	NPC151214
0.913	High Similarity	NPC175
0.913	High Similarity	NPC191915
0.9043	High Similarity	NPC233649
0.9043	High Similarity	NPC470028
0.9022	High Similarity	NPC256104
0.9022	High Similarity	NPC122083
0.9022	High Similarity	NPC182740
0.9022	High Similarity	NPC211845
0.8958	High Similarity	NPC475574
0.8936	High Similarity	NPC237071
0.8936	High Similarity	NPC252056
0.8936	High Similarity	NPC203434
0.8936	High Similarity	NPC142264
0.8936	High Similarity	NPC476510
0.8936	High Similarity	NPC238796
0.8925	High Similarity	NPC30687
0.8913	High Similarity	NPC59006
0.8817	High Similarity	NPC167644
0.8817	High Similarity	NPC311246
0.8804	High Similarity	NPC473542
0.8778	High Similarity	NPC155531
0.8778	High Similarity	NPC215968
0.8737	High Similarity	NPC296936
0.8723	High Similarity	NPC477224
0.8723	High Similarity	NPC3538
0.8723	High Similarity	NPC45959
0.8723	High Similarity	NPC113500
0.8723	High Similarity	NPC252253
0.871	High Similarity	NPC36372
0.871	High Similarity	NPC149966
0.871	High Similarity	NPC5632
0.8696	High Similarity	NPC82955
0.8696	High Similarity	NPC102725
0.8681	High Similarity	NPC210658
0.8681	High Similarity	NPC161928
0.8667	High Similarity	NPC273290
0.8667	High Similarity	NPC232044
0.8652	High Similarity	NPC477285
0.8652	High Similarity	NPC111582
0.8646	High Similarity	NPC475207
0.8646	High Similarity	NPC210157
0.8646	High Similarity	NPC470591
0.8632	High Similarity	NPC474399
0.8632	High Similarity	NPC57964
0.8632	High Similarity	NPC94582
0.8632	High Similarity	NPC21897
0.8617	High Similarity	NPC144790
0.8617	High Similarity	NPC88962
0.8617	High Similarity	NPC149400
0.8617	High Similarity	NPC473726
0.8617	High Similarity	NPC277774
0.8602	High Similarity	NPC223143
0.8602	High Similarity	NPC279329
0.8587	High Similarity	NPC128475
0.8587	High Similarity	NPC281004
0.8571	High Similarity	NPC477283
0.8557	High Similarity	NPC292775
0.8556	High Similarity	NPC227260
0.8542	High Similarity	NPC139271
0.8542	High Similarity	NPC304011
0.8539	High Similarity	NPC296734
0.8539	High Similarity	NPC470611
0.8539	High Similarity	NPC286719
0.8539	High Similarity	NPC477286
0.8539	High Similarity	NPC475388
0.8526	High Similarity	NPC475436
0.8526	High Similarity	NPC253268
0.8526	High Similarity	NPC24960
0.8526	High Similarity	NPC309866
0.8526	High Similarity	NPC174024
0.8526	High Similarity	NPC473774
0.8526	High Similarity	NPC291547
0.8526	High Similarity	NPC312678
0.8526	High Similarity	NPC179859
0.8526	High Similarity	NPC473851
0.8526	High Similarity	NPC131693
0.8511	High Similarity	NPC229801
0.8511	High Similarity	NPC307167
0.8511	High Similarity	NPC210759
0.8511	High Similarity	NPC293609
0.8495	Intermediate Similarity	NPC20822
0.8495	Intermediate Similarity	NPC473472
0.8478	Intermediate Similarity	NPC43912
0.8478	Intermediate Similarity	NPC140446
0.8478	Intermediate Similarity	NPC5943
0.8469	Intermediate Similarity	NPC41843
0.8462	Intermediate Similarity	NPC266651
0.8462	Intermediate Similarity	NPC290612
0.8454	Intermediate Similarity	NPC274200
0.8454	Intermediate Similarity	NPC477223
0.8454	Intermediate Similarity	NPC477222
0.8438	Intermediate Similarity	NPC92196
0.8427	Intermediate Similarity	NPC190940
0.8421	Intermediate Similarity	NPC477451
0.8421	Intermediate Similarity	NPC249204
0.8421	Intermediate Similarity	NPC477547
0.8421	Intermediate Similarity	NPC250393
0.8421	Intermediate Similarity	NPC234352
0.8421	Intermediate Similarity	NPC177834
0.8421	Intermediate Similarity	NPC325828
0.8421	Intermediate Similarity	NPC297348
0.8421	Intermediate Similarity	NPC141769
0.8421	Intermediate Similarity	NPC48339
0.8404	Intermediate Similarity	NPC65550
0.837	Intermediate Similarity	NPC471240
0.837	Intermediate Similarity	NPC131365
0.837	Intermediate Similarity	NPC471411
0.837	Intermediate Similarity	NPC471410
0.8367	Intermediate Similarity	NPC473638
0.8352	Intermediate Similarity	NPC474156
0.8351	Intermediate Similarity	NPC473287
0.8351	Intermediate Similarity	NPC121453
0.8333	Intermediate Similarity	NPC294686
0.8333	Intermediate Similarity	NPC475325
0.8333	Intermediate Similarity	NPC222731
0.8333	Intermediate Similarity	NPC305418
0.8333	Intermediate Similarity	NPC471464
0.8333	Intermediate Similarity	NPC217205
0.8333	Intermediate Similarity	NPC291203
0.8333	Intermediate Similarity	NPC473503
0.8333	Intermediate Similarity	NPC264101
0.8316	Intermediate Similarity	NPC473637
0.8316	Intermediate Similarity	NPC204881
0.8316	Intermediate Similarity	NPC476668
0.8316	Intermediate Similarity	NPC473830
0.8315	Intermediate Similarity	NPC7479
0.8315	Intermediate Similarity	NPC257296
0.8315	Intermediate Similarity	NPC248944
0.8298	Intermediate Similarity	NPC131466
0.8265	Intermediate Similarity	NPC476112
0.8265	Intermediate Similarity	NPC307534
0.8252	Intermediate Similarity	NPC472079
0.8247	Intermediate Similarity	NPC473610
0.8247	Intermediate Similarity	NPC107962
0.8247	Intermediate Similarity	NPC206003
0.8247	Intermediate Similarity	NPC6295
0.8247	Intermediate Similarity	NPC475351
0.8247	Intermediate Similarity	NPC469710
0.8247	Intermediate Similarity	NPC215570
0.8247	Intermediate Similarity	NPC19400
0.8247	Intermediate Similarity	NPC473727
0.8247	Intermediate Similarity	NPC211354
0.8247	Intermediate Similarity	NPC107188
0.8242	Intermediate Similarity	NPC470070
0.8229	Intermediate Similarity	NPC137004
0.8229	Intermediate Similarity	NPC172838
0.8229	Intermediate Similarity	NPC476669
0.8222	Intermediate Similarity	NPC73515
0.8202	Intermediate Similarity	NPC476176
0.8202	Intermediate Similarity	NPC477287
0.82	Intermediate Similarity	NPC178853
0.82	Intermediate Similarity	NPC477225
0.82	Intermediate Similarity	NPC477172
0.8191	Intermediate Similarity	NPC56777
0.8191	Intermediate Similarity	NPC201607
0.819	Intermediate Similarity	NPC473062
0.8182	Intermediate Similarity	NPC473518
0.8182	Intermediate Similarity	NPC291548
0.8182	Intermediate Similarity	NPC473616
0.8173	Intermediate Similarity	NPC227879
0.8173	Intermediate Similarity	NPC473570
0.8173	Intermediate Similarity	NPC208333
0.8172	Intermediate Similarity	NPC114378
0.8172	Intermediate Similarity	NPC103782
0.8163	Intermediate Similarity	NPC470864
0.8163	Intermediate Similarity	NPC470865
0.8163	Intermediate Similarity	NPC475643
0.8163	Intermediate Similarity	NPC470866
0.8163	Intermediate Similarity	NPC128572
0.8163	Intermediate Similarity	NPC116683
0.8163	Intermediate Similarity	NPC103616
0.8163	Intermediate Similarity	NPC30856
0.8163	Intermediate Similarity	NPC98018
0.8163	Intermediate Similarity	NPC470863
0.8163	Intermediate Similarity	NPC132080
0.8163	Intermediate Similarity	NPC116756
0.8163	Intermediate Similarity	NPC473601
0.8163	Intermediate Similarity	NPC284104
0.8163	Intermediate Similarity	NPC84111
0.8163	Intermediate Similarity	NPC232037
0.8163	Intermediate Similarity	NPC97700

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 NPC156377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	510
0.1-0.2	4232
0.2-0.3	3104
0.3-0.4	710
0.4-0.5	335
0.5-0.6	183
0.6-0.7	60
0.7-0.8	14
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD8171	Discontinued
0.8315	Intermediate Similarity	NPD6928	Phase 2
0.7961	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8377	Approved
0.7456	Intermediate Similarity	NPD8294	Approved
0.7434	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD7328	Approved
0.7391	Intermediate Similarity	NPD8296	Approved
0.7391	Intermediate Similarity	NPD8335	Approved
0.7391	Intermediate Similarity	NPD8380	Approved
0.7391	Intermediate Similarity	NPD8379	Approved
0.7391	Intermediate Similarity	NPD8378	Approved
0.7391	Intermediate Similarity	NPD8033	Approved
0.7368	Intermediate Similarity	NPD7516	Approved
0.7353	Intermediate Similarity	NPD7991	Discontinued
0.7232	Intermediate Similarity	NPD8133	Approved
0.7191	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6697	Approved
0.7128	Intermediate Similarity	NPD6115	Approved
0.7128	Intermediate Similarity	NPD6118	Approved
0.7128	Intermediate Similarity	NPD6114	Approved
0.7025	Intermediate Similarity	NPD7736	Approved
0.7021	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD7507	Approved
0.6915	Remote Similarity	NPD6117	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.681	Remote Similarity	NPD6940	Discontinued
0.6807	Remote Similarity	NPD7503	Approved
0.6803	Remote Similarity	NPD8293	Discontinued
0.6777	Remote Similarity	NPD7492	Approved
0.6726	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6054	Approved
0.6723	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6616	Approved
0.6702	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1700	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD7078	Approved
0.6632	Remote Similarity	NPD3702	Approved
0.6612	Remote Similarity	NPD6370	Approved
0.66	Remote Similarity	NPD3669	Approved
0.66	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8034	Phase 2
0.6571	Remote Similarity	NPD8035	Phase 2
0.6559	Remote Similarity	NPD4787	Phase 1
0.6559	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6015	Approved
0.6529	Remote Similarity	NPD6016	Approved
0.6526	Remote Similarity	NPD1811	Approved
0.6526	Remote Similarity	NPD1810	Approved
0.6475	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7638	Approved
0.6348	Remote Similarity	NPD8174	Phase 2
0.6333	Remote Similarity	NPD6009	Approved
0.6316	Remote Similarity	NPD5777	Approved
0.6316	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6319	Approved
0.6311	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7640	Approved
0.6306	Remote Similarity	NPD7639	Approved
0.6289	Remote Similarity	NPD3703	Phase 2
0.6271	Remote Similarity	NPD8297	Approved
0.6271	Remote Similarity	NPD6882	Approved
0.6264	Remote Similarity	NPD371	Approved
0.6228	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6033	Approved
0.6218	Remote Similarity	NPD4632	Approved
0.6211	Remote Similarity	NPD2254	Approved
0.6211	Remote Similarity	NPD4244	Approved
0.6211	Remote Similarity	NPD4245	Approved
0.6211	Remote Similarity	NPD2686	Approved
0.6211	Remote Similarity	NPD2687	Approved
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7632	Discontinued
0.6174	Remote Similarity	NPD6402	Approved
0.6174	Remote Similarity	NPD5739	Approved
0.6174	Remote Similarity	NPD6008	Approved
0.6174	Remote Similarity	NPD7128	Approved
0.6174	Remote Similarity	NPD6675	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.616	Remote Similarity	NPD6067	Discontinued
0.616	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7525	Registered
0.6105	Remote Similarity	NPD3698	Phase 2
0.6105	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD1780	Approved
0.6078	Remote Similarity	NPD1779	Approved
0.6068	Remote Similarity	NPD6899	Approved
0.6068	Remote Similarity	NPD6686	Approved
0.6068	Remote Similarity	NPD6881	Approved
0.605	Remote Similarity	NPD8130	Phase 1
0.6018	Remote Similarity	NPD8418	Phase 2
0.6017	Remote Similarity	NPD6373	Approved
0.6017	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5360	Phase 3
0.6	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5701	Approved
0.5983	Remote Similarity	NPD5697	Approved
0.5979	Remote Similarity	NPD6081	Approved
0.5966	Remote Similarity	NPD7102	Approved
0.5966	Remote Similarity	NPD7290	Approved
0.5966	Remote Similarity	NPD6883	Approved
0.5946	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7115	Discovery
0.5929	Remote Similarity	NPD7625	Phase 1
0.5917	Remote Similarity	NPD6649	Approved
0.5917	Remote Similarity	NPD6869	Approved
0.5917	Remote Similarity	NPD6650	Approved
0.5917	Remote Similarity	NPD6617	Approved
0.5917	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD8449	Approved
0.5882	Remote Similarity	NPD6013	Approved
0.5882	Remote Similarity	NPD6012	Approved
0.5882	Remote Similarity	NPD6014	Approved
0.5876	Remote Similarity	NPD4789	Approved
0.5873	Remote Similarity	NPD5983	Phase 2
0.5865	Remote Similarity	NPD8450	Suspended
0.5854	Remote Similarity	NPD7754	Approved
0.5854	Remote Similarity	NPD7755	Approved
0.5847	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6084	Phase 2
0.5841	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD4634	Approved
0.5833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6336	Discontinued
0.5798	Remote Similarity	NPD6011	Approved
0.5789	Remote Similarity	NPD4224	Phase 2
0.5785	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4802	Phase 2
0.5784	Remote Similarity	NPD4238	Approved
0.5766	Remote Similarity	NPD6399	Phase 3
0.5758	Remote Similarity	NPD5956	Approved
0.5741	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD7748	Approved
0.5702	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD4755	Approved
0.569	Remote Similarity	NPD4159	Approved
0.5684	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4788	Approved
0.5657	Remote Similarity	NPD4758	Discontinued
0.5652	Remote Similarity	NPD4225	Approved
0.5648	Remote Similarity	NPD8308	Discontinued
0.5636	Remote Similarity	NPD6051	Approved
0.5631	Remote Similarity	NPD3671	Phase 1
0.5631	Remote Similarity	NPD5364	Discontinued
0.5625	Remote Similarity	NPD8515	Approved
0.5625	Remote Similarity	NPD8516	Approved
0.5625	Remote Similarity	NPD4202	Approved
0.5625	Remote Similarity	NPD8517	Approved
0.5625	Remote Similarity	NPD8513	Phase 3
0.5625	Remote Similarity	NPD6921	Approved
0.5607	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD4700	Approved
0.5603	Remote Similarity	NPD5286	Approved
0.5603	Remote Similarity	NPD5285	Approved
0.5603	Remote Similarity	NPD4696	Approved
0.56	Remote Similarity	NPD6274	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