NPASS Compound

Structure

NPC472574 OpenBabel07101719512D 46 51 0 0 1 0 0 0 0 0999 V2000 1.1135 -0.4915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9621 4.3489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9165 0.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2719 -0.7092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0494 0.7371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9672 3.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9773 7.0515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1187 3.5062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9672 2.0365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0410 6.7627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6955 6.3850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2701 3.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1187 1.5466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8230 5.8074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4775 5.4298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0808 3.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4144 4.5852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7246 0.8411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7369 1.8295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1135 0.4883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9621 3.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2701 2.0365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5413 5.1410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0431 1.1939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7246 1.5466 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0491 1.9865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6036 3.0113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5253 4.1734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1421 1.5790 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1135 1.8994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4216 1.5466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1052 3.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9552 0.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5025 1.5466 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5025 0.8411 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6423 3.2006 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8106 2.8792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0155 2.1222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3304 4.6505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4216 0.5668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8234 2.5641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1135 2.8792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5731 2.0365 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1689 2.9418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0759 2.5342 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 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 35 1 1 0 0 0 21 37 2 0 0 0 0 21 42 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 19 1 6 0 0 0 24 29 1 0 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 25 43 1 1 0 0 0 26 34 1 6 0 0 0 26 44 1 0 0 0 0 27 36 1 0 0 0 0 27 38 2 0 0 0 0 28 36 1 0 0 0 0 28 39 2 0 0 0 0 29 35 1 1 0 0 0 29 45 1 0 0 0 0 30 34 1 1 0 0 0 30 42 1 0 0 0 0 31 40 2 0 0 0 0 31 43 1 0 0 0 0 32 41 2 0 0 0 0 32 44 1 0 0 0 0 33 46 1 0 0 0 0 34 35 1 6 0 0 0 35 46 1 6 0 0 0 36 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	633.26
Volume:	632.475
LogP:	4.953
LogD:	3.877
LogS:	-4.252
# Rotatable Bonds:	10
TPSA:	142.75
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	6.014
Fsp3:	0.457
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:	-5.279
MDCK Permeability:	3.2243551686406136e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	100.14376068115234%
Volume Distribution (VD):	1.078
Pgp-substrate:	4.518194675445557%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.183
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.225
CYP2D6-inhibitor:	0.915
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.677
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	5.684
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.95
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.059
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.168
Respiratory Toxicity:	0.493

Download Data

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

Natural Product: NPC472574

Natural Product ID:	NPC472574
*Common Name:**	CEBQOGCIDLLPPG-LPWRDBNFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CEBQOGCIDLLPPG-LPWRDBNFSA-N
Standard InCHI:	InChI=1S/C35H39NO10/c1-20-18-25(43-31(40)22-12-8-6-9-13-22)30(42-21(2)37)34(5)26(44-32(41)23-14-10-7-11-15-23)19-24-29(35(20,34)46-33(24,3)4)45-36-27(38)16-17-28(36)39/h6-15,20,24-26,29-30H,16-19H2,1-5H3/t20-,24-,25+,26+,29-,30+,34-,35-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@@H](OC(=O)c2ccccc2)C[C@H]([C@@]23[C@]1(C)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3ON1C(=O)CCC1=O)C(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577218
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	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
Ki	1
Others	9

Activity Type	# Activity
Individual Protein	8
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	=	75.4	%	PMID[550691]
NPT27	Others	Unspecified		Activity	=	70.2	%	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	54.9	n.a.	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	33.6	n.a.	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	21.7	n.a.	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	17.3	n.a.	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	13.1	n.a.	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	6.9	n.a.	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	290.0	nM	PMID[550691]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	80.1	%	PMID[550691]

☑ 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 NPC472574 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	295
0.1-0.2	1170
0.2-0.3	2449
0.3-0.4	5946
0.4-0.5	13605
0.5-0.6	15655
0.6-0.7	2988
0.7-0.8	432
0.8-0.85	131
0.85-0.9	25
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8733	High Similarity	NPC473112
0.8733	High Similarity	NPC48017
0.8733	High Similarity	NPC473085
0.8733	High Similarity	NPC4341
0.8733	High Similarity	NPC473060
0.8733	High Similarity	NPC476094
0.8733	High Similarity	NPC473613
0.8733	High Similarity	NPC211137
0.8733	High Similarity	NPC43241
0.8733	High Similarity	NPC473758
0.8733	High Similarity	NPC184747
0.8733	High Similarity	NPC473081
0.8733	High Similarity	NPC200592
0.8733	High Similarity	NPC147880
0.8733	High Similarity	NPC473109
0.8667	High Similarity	NPC475652
0.8667	High Similarity	NPC210591
0.8667	High Similarity	NPC214550
0.86	High Similarity	NPC183122
0.86	High Similarity	NPC283375
0.8562	High Similarity	NPC191082
0.8562	High Similarity	NPC475429
0.8562	High Similarity	NPC139067
0.8562	High Similarity	NPC177340
0.8562	High Similarity	NPC270498
0.8562	High Similarity	NPC147217
0.8562	High Similarity	NPC246480
0.8562	High Similarity	NPC473673
0.8506	High Similarity	NPC188865
0.8506	High Similarity	NPC95265
0.8506	High Similarity	NPC472570
0.8506	High Similarity	NPC472573
0.8506	High Similarity	NPC125106
0.8506	High Similarity	NPC51314
0.8506	High Similarity	NPC67777
0.8506	High Similarity	NPC95810
0.8506	High Similarity	NPC11685
0.8506	High Similarity	NPC472569
0.8506	High Similarity	NPC70716
0.8506	High Similarity	NPC57628
0.8506	High Similarity	NPC470231
0.8506	High Similarity	NPC25768
0.8506	High Similarity	NPC476974
0.8506	High Similarity	NPC163719
0.8467	Intermediate Similarity	NPC291638
0.8467	Intermediate Similarity	NPC17877
0.8467	Intermediate Similarity	NPC195647
0.8467	Intermediate Similarity	NPC66761
0.8467	Intermediate Similarity	NPC472577
0.8452	Intermediate Similarity	NPC174982
0.8452	Intermediate Similarity	NPC470159
0.8452	Intermediate Similarity	NPC96903
0.8452	Intermediate Similarity	NPC158663
0.8452	Intermediate Similarity	NPC184817
0.8452	Intermediate Similarity	NPC476973
0.8452	Intermediate Similarity	NPC177940
0.8452	Intermediate Similarity	NPC469349
0.8452	Intermediate Similarity	NPC471104
0.8452	Intermediate Similarity	NPC473088
0.8452	Intermediate Similarity	NPC29704
0.8452	Intermediate Similarity	NPC70403
0.8452	Intermediate Similarity	NPC171525
0.8452	Intermediate Similarity	NPC472568
0.8452	Intermediate Similarity	NPC472571
0.8452	Intermediate Similarity	NPC200471
0.8452	Intermediate Similarity	NPC472572
0.8452	Intermediate Similarity	NPC472575
0.8452	Intermediate Similarity	NPC470157
0.8442	Intermediate Similarity	NPC163087
0.84	Intermediate Similarity	NPC474608
0.8387	Intermediate Similarity	NPC475759
0.8387	Intermediate Similarity	NPC470152
0.8387	Intermediate Similarity	NPC241951
0.8387	Intermediate Similarity	NPC475122
0.8344	Intermediate Similarity	NPC281717
0.8312	Intermediate Similarity	NPC16912
0.8291	Intermediate Similarity	NPC476975
0.8291	Intermediate Similarity	NPC270590
0.8291	Intermediate Similarity	NPC266265
0.8291	Intermediate Similarity	NPC92293
0.8291	Intermediate Similarity	NPC301556
0.8291	Intermediate Similarity	NPC471101
0.828	Intermediate Similarity	NPC474935
0.8253	Intermediate Similarity	NPC30171
0.8247	Intermediate Similarity	NPC171207
0.8247	Intermediate Similarity	NPC90614
0.8247	Intermediate Similarity	NPC97667
0.8239	Intermediate Similarity	NPC254558
0.8239	Intermediate Similarity	NPC470245
0.8239	Intermediate Similarity	NPC473214
0.8217	Intermediate Similarity	NPC472556
0.8194	Intermediate Similarity	NPC97947
0.8194	Intermediate Similarity	NPC472576
0.8194	Intermediate Similarity	NPC27377
0.8194	Intermediate Similarity	NPC87448
0.8194	Intermediate Similarity	NPC41481
0.8194	Intermediate Similarity	NPC291599
0.8194	Intermediate Similarity	NPC118080
0.8187	Intermediate Similarity	NPC470153
0.8182	Intermediate Similarity	NPC253738
0.8176	Intermediate Similarity	NPC473215
0.8133	Intermediate Similarity	NPC147561
0.8129	Intermediate Similarity	NPC477904
0.8129	Intermediate Similarity	NPC183270
0.8129	Intermediate Similarity	NPC275592
0.8129	Intermediate Similarity	NPC100913
0.8117	Intermediate Similarity	NPC475373
0.8077	Intermediate Similarity	NPC224491
0.8037	Intermediate Similarity	NPC34066
0.8037	Intermediate Similarity	NPC282239
0.8025	Intermediate Similarity	NPC477905
0.8012	Intermediate Similarity	NPC31829
0.7988	Intermediate Similarity	NPC106895
0.7987	Intermediate Similarity	NPC471100
0.7987	Intermediate Similarity	NPC471107
0.7939	Intermediate Similarity	NPC472393
0.7937	Intermediate Similarity	NPC473602
0.7937	Intermediate Similarity	NPC48599
0.7937	Intermediate Similarity	NPC209592
0.7927	Intermediate Similarity	NPC469422
0.7914	Intermediate Similarity	NPC472548
0.7911	Intermediate Similarity	NPC34012
0.7901	Intermediate Similarity	NPC112216
0.7898	Intermediate Similarity	NPC472547
0.7892	Intermediate Similarity	NPC471102
0.7888	Intermediate Similarity	NPC473760
0.7879	Intermediate Similarity	NPC217091
0.7867	Intermediate Similarity	NPC473082
0.7867	Intermediate Similarity	NPC473111
0.7867	Intermediate Similarity	NPC473110
0.7866	Intermediate Similarity	NPC77719
0.7862	Intermediate Similarity	NPC91703
0.7853	Intermediate Similarity	NPC51602
0.7848	Intermediate Similarity	NPC266374
0.7844	Intermediate Similarity	NPC477623
0.7834	Intermediate Similarity	NPC472395
0.7834	Intermediate Similarity	NPC472371
0.7826	Intermediate Similarity	NPC240115
0.7821	Intermediate Similarity	NPC472545
0.7821	Intermediate Similarity	NPC472551
0.7818	Intermediate Similarity	NPC472549
0.7818	Intermediate Similarity	NPC112523
0.7818	Intermediate Similarity	NPC114410
0.7818	Intermediate Similarity	NPC228204
0.7818	Intermediate Similarity	NPC26033
0.78	Intermediate Similarity	NPC114927
0.78	Intermediate Similarity	NPC473083
0.7799	Intermediate Similarity	NPC472546
0.7791	Intermediate Similarity	NPC165260
0.7791	Intermediate Similarity	NPC7095
0.7791	Intermediate Similarity	NPC161239
0.7791	Intermediate Similarity	NPC469448
0.7791	Intermediate Similarity	NPC198455
0.7785	Intermediate Similarity	NPC475400
0.7771	Intermediate Similarity	NPC39549
0.7771	Intermediate Similarity	NPC326235
0.7771	Intermediate Similarity	NPC323001
0.7758	Intermediate Similarity	NPC242262
0.7758	Intermediate Similarity	NPC473414
0.7758	Intermediate Similarity	NPC237549
0.7758	Intermediate Similarity	NPC472658
0.7758	Intermediate Similarity	NPC256142
0.7758	Intermediate Similarity	NPC472030
0.7758	Intermediate Similarity	NPC158333
0.7758	Intermediate Similarity	NPC304876
0.7758	Intermediate Similarity	NPC472005
0.7758	Intermediate Similarity	NPC472657
0.7758	Intermediate Similarity	NPC472022
0.7758	Intermediate Similarity	NPC249471
0.7758	Intermediate Similarity	NPC257213
0.7758	Intermediate Similarity	NPC1173
0.7758	Intermediate Similarity	NPC265395
0.7756	Intermediate Similarity	NPC473216
0.7756	Intermediate Similarity	NPC473399
0.775	Intermediate Similarity	NPC477894
0.775	Intermediate Similarity	NPC191387
0.775	Intermediate Similarity	NPC131966
0.7744	Intermediate Similarity	NPC469415
0.7744	Intermediate Similarity	NPC471103
0.773	Intermediate Similarity	NPC60509
0.773	Intermediate Similarity	NPC250046
0.773	Intermediate Similarity	NPC81698
0.773	Intermediate Similarity	NPC76103
0.7725	Intermediate Similarity	NPC318447
0.7725	Intermediate Similarity	NPC322048
0.7711	Intermediate Similarity	NPC469398
0.7711	Intermediate Similarity	NPC473611
0.7702	Intermediate Similarity	NPC38696
0.7702	Intermediate Similarity	NPC34943
0.7692	Intermediate Similarity	NPC476077
0.7692	Intermediate Similarity	NPC48929
0.7683	Intermediate Similarity	NPC222102
0.7683	Intermediate Similarity	NPC303429
0.7679	Intermediate Similarity	NPC469399
0.7677	Intermediate Similarity	NPC472394
0.7677	Intermediate Similarity	NPC238370
0.7654	Intermediate Similarity	NPC127857
0.7654	Intermediate Similarity	NPC125882
0.7636	Intermediate Similarity	NPC96308
0.7633	Intermediate Similarity	NPC326328

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 NPC472574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	640
0.2-0.3	1205
0.3-0.4	2661
0.4-0.5	3001
0.5-0.6	1284
0.6-0.7	150
0.7-0.8	5
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
0.7401	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8407	Phase 2
0.7247	Intermediate Similarity	NPD7799	Discontinued
0.7189	Intermediate Similarity	NPD8361	Approved
0.7189	Intermediate Similarity	NPD8360	Approved
0.7189	Intermediate Similarity	NPD8435	Approved
0.7134	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7239	Suspended
0.7088	Intermediate Similarity	NPD8368	Discontinued
0.7081	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8485	Approved
0.7024	Intermediate Similarity	NPD7236	Approved
0.7019	Intermediate Similarity	NPD7713	Phase 3
0.7	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7497	Discontinued
0.6898	Remote Similarity	NPD8434	Phase 2
0.6872	Remote Similarity	NPD8127	Discontinued
0.6815	Remote Similarity	NPD6287	Discontinued
0.6755	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8150	Discontinued
0.6687	Remote Similarity	NPD7008	Discontinued
0.6685	Remote Similarity	NPD7177	Discontinued
0.6683	Remote Similarity	NPD6997	Phase 2
0.6633	Remote Similarity	NPD8320	Phase 1
0.6633	Remote Similarity	NPD8319	Approved
0.6612	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7715	Approved
0.6606	Remote Similarity	NPD7714	Approved
0.6606	Remote Similarity	NPD7961	Discontinued
0.6584	Remote Similarity	NPD5667	Approved
0.6579	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8462	Phase 1
0.6556	Remote Similarity	NPD4967	Phase 2
0.6556	Remote Similarity	NPD4966	Approved
0.6556	Remote Similarity	NPD7058	Phase 2
0.6556	Remote Similarity	NPD4965	Approved
0.6556	Remote Similarity	NPD7057	Phase 3
0.6548	Remote Similarity	NPD2567	Approved
0.6548	Remote Similarity	NPD2569	Approved
0.6541	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6386	Approved
0.6517	Remote Similarity	NPD6873	Phase 2
0.6517	Remote Similarity	NPD6385	Approved
0.6514	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6273	Approved
0.6512	Remote Similarity	NPD8166	Discontinued
0.6505	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7699	Phase 2
0.6497	Remote Similarity	NPD7700	Phase 2
0.6495	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6234	Discontinued
0.6474	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5844	Phase 1
0.6465	Remote Similarity	NPD8285	Discontinued
0.6457	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7701	Phase 2
0.6453	Remote Similarity	NPD7179	Phase 2
0.6448	Remote Similarity	NPD5494	Approved
0.6447	Remote Similarity	NPD2182	Approved
0.6446	Remote Similarity	NPD3764	Approved
0.6443	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8404	Phase 2
0.6429	Remote Similarity	NPD6535	Approved
0.6429	Remote Similarity	NPD6534	Approved
0.6417	Remote Similarity	NPD7228	Approved
0.6416	Remote Similarity	NPD4628	Phase 3
0.6404	Remote Similarity	NPD7458	Discontinued
0.6394	Remote Similarity	NPD7047	Phase 3
0.639	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.639	Remote Similarity	NPD7874	Approved
0.6389	Remote Similarity	NPD7248	Discontinued
0.6389	Remote Similarity	NPD37	Approved
0.6386	Remote Similarity	NPD6039	Approved
0.6384	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD2438	Suspended
0.6369	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6310	Approved
0.6369	Remote Similarity	NPD6311	Approved
0.6369	Remote Similarity	NPD6309	Approved
0.6364	Remote Similarity	NPD7473	Discontinued
0.6364	Remote Similarity	NPD5204	Approved
0.6355	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7819	Suspended
0.6354	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD7741	Discontinued
0.6344	Remote Similarity	NPD5242	Approved
0.634	Remote Similarity	NPD7693	Approved
0.6337	Remote Similarity	NPD7696	Phase 3
0.6337	Remote Similarity	NPD7697	Approved
0.6337	Remote Similarity	NPD7698	Approved
0.6337	Remote Similarity	NPD7435	Discontinued
0.6326	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD8059	Phase 3
0.6322	Remote Similarity	NPD7003	Approved
0.6319	Remote Similarity	NPD5353	Approved
0.6308	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5951	Approved
0.6305	Remote Similarity	NPD7870	Phase 2
0.6305	Remote Similarity	NPD7871	Phase 2
0.6304	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD8313	Approved
0.6302	Remote Similarity	NPD8312	Approved
0.6294	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6232	Discontinued
0.6286	Remote Similarity	NPD6190	Approved
0.6284	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7768	Phase 2
0.6284	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7240	Approved
0.6282	Remote Similarity	NPD6858	Approved
0.6282	Remote Similarity	NPD7094	Approved
0.628	Remote Similarity	NPD2198	Approved
0.628	Remote Similarity	NPD7801	Approved
0.628	Remote Similarity	NPD2199	Approved
0.6269	Remote Similarity	NPD6780	Approved
0.6269	Remote Similarity	NPD6782	Approved
0.6269	Remote Similarity	NPD6779	Approved
0.6269	Remote Similarity	NPD6778	Approved
0.6269	Remote Similarity	NPD6781	Approved
0.6269	Remote Similarity	NPD6777	Approved
0.6269	Remote Similarity	NPD6776	Approved
0.6269	Remote Similarity	NPD4107	Approved
0.6266	Remote Similarity	NPD4198	Discontinued
0.6265	Remote Similarity	NPD3663	Approved
0.6265	Remote Similarity	NPD3661	Approved
0.6265	Remote Similarity	NPD3664	Approved
0.6265	Remote Similarity	NPD3662	Phase 3
0.6258	Remote Similarity	NPD6637	Approved
0.625	Remote Similarity	NPD4420	Approved
0.6244	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7611	Approved
0.6243	Remote Similarity	NPD6677	Suspended
0.623	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD2575	Approved
0.6221	Remote Similarity	NPD3748	Approved
0.6207	Remote Similarity	NPD5005	Approved
0.6207	Remote Similarity	NPD6823	Phase 2
0.6207	Remote Similarity	NPD5006	Approved
0.6203	Remote Similarity	NPD2629	Approved
0.6198	Remote Similarity	NPD7039	Approved
0.6198	Remote Similarity	NPD7038	Approved
0.6196	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7999	Approved
0.6193	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6599	Discontinued
0.6184	Remote Similarity	NPD164	Approved
0.6184	Remote Similarity	NPD8151	Discontinued
0.618	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3373	Approved
0.6176	Remote Similarity	NPD2979	Phase 3
0.6176	Remote Similarity	NPD5120	Approved
0.6176	Remote Similarity	NPD5121	Approved
0.6176	Remote Similarity	NPD5119	Approved
0.6175	Remote Similarity	NPD8455	Phase 2
0.6175	Remote Similarity	NPD5761	Phase 2
0.6175	Remote Similarity	NPD5760	Phase 2
0.6175	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5125	Phase 3
0.6173	Remote Similarity	NPD5126	Approved
0.6173	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7583	Approved
0.6162	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7075	Discontinued
0.6158	Remote Similarity	NPD4482	Phase 3
0.6154	Remote Similarity	NPD4619	Approved
0.6154	Remote Similarity	NPD4621	Approved
0.6141	Remote Similarity	NPD5402	Approved
0.6141	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4481	Phase 3
0.6136	Remote Similarity	NPD4110	Phase 3
0.6136	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7585	Approved
0.6133	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD1238	Approved
0.6133	Remote Similarity	NPD3226	Approved
0.6131	Remote Similarity	NPD4620	Approved
0.6131	Remote Similarity	NPD5201	Approved
0.6131	Remote Similarity	NPD6212	Phase 3
0.6131	Remote Similarity	NPD2613	Approved
0.6131	Remote Similarity	NPD4617	Approved
0.6131	Remote Similarity	NPD5203	Approved
0.6131	Remote Similarity	NPD6213	Phase 3
0.6131	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.612	Remote Similarity	NPD7011	Discontinued
0.6118	Remote Similarity	NPD6663	Approved
0.6118	Remote Similarity	NPD8032	Phase 2
0.6114	Remote Similarity	NPD7685	Pre-registration
0.6114	Remote Similarity	NPD6765	Approved
0.6114	Remote Similarity	NPD6764	Approved
0.6111	Remote Similarity	NPD5525	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