NPASS Compound

Structure

NPC140021 OpenBabel07101719252D 40 44 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5663 3.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4242 2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.6235 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 -4.1123 -1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3438 3.0125 0.0000 C 0 0 0 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 1.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5139 1.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 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 -4.0017 2.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7470 -2.1137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9977 2.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2954 0.1738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 18 2 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 19 2 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 22 1 0 0 0 0 17 34 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 0 0 0 0 20 29 1 0 0 0 0 20 32 1 6 0 0 0 23 14 1 1 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 32 1 1 0 0 0 25 28 1 0 0 0 0 25 32 1 6 0 0 0 26 35 2 0 0 0 0 26 40 1 0 0 0 0 27 36 2 0 0 0 0 28 31 1 0 0 0 0 28 33 1 6 0 0 0 29 33 1 1 0 0 0 29 39 1 0 0 0 0 30 37 2 0 0 0 0 30 39 1 0 0 0 0 31 33 1 0 0 0 0 32 38 1 6 0 0 0 33 40 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.28
Volume:	574.345
LogP:	4.1
LogD:	3.485
LogS:	-5.023
# Rotatable Bonds:	8
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	5.091
Fsp3:	0.545
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:	-4.815
MDCK Permeability:	1.652540231589228e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	85.36308288574219%
Volume Distribution (VD):	0.929
Pgp-substrate:	8.652566909790039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.837
CYP2C19-substrate:	0.424
CYP2C9-inhibitor:	0.951
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.506
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	9.644
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.859
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.736
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.433
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC140021

Natural Product ID:	NPC140021
*Common Name:**	QQWKSYBTCMDQAG-WJGWMERZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QQWKSYBTCMDQAG-WJGWMERZSA-N
Standard InCHI:	InChI=1S/C33H40O7/c1-7-18(2)30(37)39-29-20(4)32(38)24-13-19(3)27(36)23(24)14-22(17-34)15-25(32)28-31(5,6)33(28,29)40-26(35)16-21-11-9-8-10-12-21/h7-13,15,20,23-25,28-29,34,38H,14,16-17H2,1-6H3/b18-7+/t20-,23-,24-,25+,28-,29-,32+,33-/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)Cc1ccccc1)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375789
PubChem CID:	73356430
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

*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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT890	Cell Line	SNU-387	Homo sapiens	IC50	>	10000.0	nM	PMID[527168]

☑ 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 NPC140021 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	293
0.1-0.2	1037
0.2-0.3	2274
0.3-0.4	4759
0.4-0.5	8707
0.5-0.6	13702
0.6-0.7	10448
0.7-0.8	1264
0.8-0.85	187
0.85-0.9	11
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9366	High Similarity	NPC283875
0.9366	High Similarity	NPC469647
0.9366	High Similarity	NPC469648
0.9366	High Similarity	NPC138641
0.9366	High Similarity	NPC22571
0.9357	High Similarity	NPC132652
0.9231	High Similarity	NPC145649
0.9231	High Similarity	NPC233581
0.9172	High Similarity	NPC11410
0.9161	High Similarity	NPC472398
0.8865	High Similarity	NPC183540
0.8803	High Similarity	NPC95449
0.8741	High Similarity	NPC34943
0.8716	High Similarity	NPC251139
0.8681	High Similarity	NPC125882
0.8671	High Similarity	NPC477894
0.8621	High Similarity	NPC240115
0.8621	High Similarity	NPC20255
0.8601	High Similarity	NPC192658
0.8592	High Similarity	NPC87934
0.8592	High Similarity	NPC162613
0.8592	High Similarity	NPC100913
0.8592	High Similarity	NPC275592
0.8592	High Similarity	NPC90614
0.8591	High Similarity	NPC471176
0.8552	High Similarity	NPC92867
0.8552	High Similarity	NPC311825
0.8531	High Similarity	NPC27377
0.8531	High Similarity	NPC291599
0.8531	High Similarity	NPC41481
0.8531	High Similarity	NPC472576
0.8531	High Similarity	NPC87448
0.8531	High Similarity	NPC118080
0.8531	High Similarity	NPC16912
0.8531	High Similarity	NPC97947
0.8521	High Similarity	NPC9905
0.8493	Intermediate Similarity	NPC312393
0.8493	Intermediate Similarity	NPC473602
0.8489	Intermediate Similarity	NPC80599
0.8483	Intermediate Similarity	NPC475122
0.8478	Intermediate Similarity	NPC472388
0.8472	Intermediate Similarity	NPC34012
0.8462	Intermediate Similarity	NPC472547
0.8462	Intermediate Similarity	NPC97667
0.8462	Intermediate Similarity	NPC171207
0.8456	Intermediate Similarity	NPC473082
0.8451	Intermediate Similarity	NPC39549
0.844	Intermediate Similarity	NPC477893
0.8435	Intermediate Similarity	NPC473760
0.8425	Intermediate Similarity	NPC470159
0.8425	Intermediate Similarity	NPC472568
0.8425	Intermediate Similarity	NPC472556
0.8425	Intermediate Similarity	NPC469349
0.8425	Intermediate Similarity	NPC471104
0.8425	Intermediate Similarity	NPC473088
0.8425	Intermediate Similarity	NPC301946
0.8425	Intermediate Similarity	NPC472575
0.8425	Intermediate Similarity	NPC134131
0.8425	Intermediate Similarity	NPC200471
0.8425	Intermediate Similarity	NPC29704
0.8425	Intermediate Similarity	NPC472571
0.8425	Intermediate Similarity	NPC472572
0.8425	Intermediate Similarity	NPC158663
0.8425	Intermediate Similarity	NPC470157
0.8425	Intermediate Similarity	NPC277053
0.8425	Intermediate Similarity	NPC184817
0.8425	Intermediate Similarity	NPC70403
0.8425	Intermediate Similarity	NPC96903
0.8425	Intermediate Similarity	NPC471162
0.8425	Intermediate Similarity	NPC174982
0.8425	Intermediate Similarity	NPC171525
0.8425	Intermediate Similarity	NPC177940
0.8425	Intermediate Similarity	NPC476973
0.8425	Intermediate Similarity	NPC25043
0.8417	Intermediate Similarity	NPC472418
0.8414	Intermediate Similarity	NPC163087
0.8406	Intermediate Similarity	NPC225103
0.8389	Intermediate Similarity	NPC51602
0.8389	Intermediate Similarity	NPC471103
0.8389	Intermediate Similarity	NPC197037
0.838	Intermediate Similarity	NPC472551
0.838	Intermediate Similarity	NPC472545
0.8378	Intermediate Similarity	NPC473215
0.8369	Intermediate Similarity	NPC474608
0.8367	Intermediate Similarity	NPC48599
0.8367	Intermediate Similarity	NPC209592
0.8367	Intermediate Similarity	NPC478263
0.8356	Intermediate Similarity	NPC11685
0.8356	Intermediate Similarity	NPC471912
0.8356	Intermediate Similarity	NPC188865
0.8356	Intermediate Similarity	NPC470152
0.8356	Intermediate Similarity	NPC472569
0.8356	Intermediate Similarity	NPC472573
0.8356	Intermediate Similarity	NPC95810
0.8356	Intermediate Similarity	NPC95265
0.8356	Intermediate Similarity	NPC25768
0.8356	Intermediate Similarity	NPC80895
0.8356	Intermediate Similarity	NPC125106
0.8356	Intermediate Similarity	NPC57628
0.8356	Intermediate Similarity	NPC241951
0.8356	Intermediate Similarity	NPC70716
0.8356	Intermediate Similarity	NPC163719
0.8356	Intermediate Similarity	NPC38696
0.8356	Intermediate Similarity	NPC475759
0.8356	Intermediate Similarity	NPC476974
0.8356	Intermediate Similarity	NPC472570
0.8345	Intermediate Similarity	NPC473443
0.8344	Intermediate Similarity	NPC469730
0.8344	Intermediate Similarity	NPC473670
0.8344	Intermediate Similarity	NPC473632
0.8344	Intermediate Similarity	NPC132599
0.8344	Intermediate Similarity	NPC21410
0.8344	Intermediate Similarity	NPC473611
0.8333	Intermediate Similarity	NPC58061
0.8333	Intermediate Similarity	NPC195224
0.8322	Intermediate Similarity	NPC125033
0.8322	Intermediate Similarity	NPC7095
0.8322	Intermediate Similarity	NPC470245
0.8322	Intermediate Similarity	NPC473214
0.8322	Intermediate Similarity	NPC91730
0.8321	Intermediate Similarity	NPC475933
0.8321	Intermediate Similarity	NPC470158
0.8311	Intermediate Similarity	NPC327031
0.8311	Intermediate Similarity	NPC217918
0.831	Intermediate Similarity	NPC17877
0.831	Intermediate Similarity	NPC291638
0.831	Intermediate Similarity	NPC477896
0.831	Intermediate Similarity	NPC472577
0.831	Intermediate Similarity	NPC195647
0.831	Intermediate Similarity	NPC66761
0.8301	Intermediate Similarity	NPC49297
0.8299	Intermediate Similarity	NPC127857
0.8299	Intermediate Similarity	NPC478264
0.8289	Intermediate Similarity	NPC106895
0.8288	Intermediate Similarity	NPC91703
0.8278	Intermediate Similarity	NPC134685
0.8278	Intermediate Similarity	NPC229545
0.8278	Intermediate Similarity	NPC248265
0.8278	Intermediate Similarity	NPC11588
0.8276	Intermediate Similarity	NPC224491
0.8276	Intermediate Similarity	NPC266374
0.8271	Intermediate Similarity	NPC329080
0.8271	Intermediate Similarity	NPC472759
0.8267	Intermediate Similarity	NPC470153
0.8264	Intermediate Similarity	NPC214550
0.8264	Intermediate Similarity	NPC475652
0.8264	Intermediate Similarity	NPC210591
0.8261	Intermediate Similarity	NPC476971
0.8261	Intermediate Similarity	NPC476972
0.8258	Intermediate Similarity	NPC477188
0.8258	Intermediate Similarity	NPC43304
0.8258	Intermediate Similarity	NPC477190
0.8255	Intermediate Similarity	NPC250046
0.8255	Intermediate Similarity	NPC60509
0.8255	Intermediate Similarity	NPC81698
0.8255	Intermediate Similarity	NPC301556
0.8255	Intermediate Similarity	NPC476975
0.8255	Intermediate Similarity	NPC270590
0.8255	Intermediate Similarity	NPC92293
0.8255	Intermediate Similarity	NPC266265
0.8255	Intermediate Similarity	NPC471101
0.8252	Intermediate Similarity	NPC472374
0.8252	Intermediate Similarity	NPC472372
0.8248	Intermediate Similarity	NPC284022
0.8248	Intermediate Similarity	NPC473083
0.8243	Intermediate Similarity	NPC474935
0.8235	Intermediate Similarity	NPC181924
0.8227	Intermediate Similarity	NPC209851
0.8227	Intermediate Similarity	NPC476976
0.8224	Intermediate Similarity	NPC26033
0.8224	Intermediate Similarity	NPC228204
0.8224	Intermediate Similarity	NPC114357
0.8224	Intermediate Similarity	NPC155329
0.8224	Intermediate Similarity	NPC259144
0.8224	Intermediate Similarity	NPC282239
0.8219	Intermediate Similarity	NPC472546
0.8219	Intermediate Similarity	NPC182869
0.8212	Intermediate Similarity	NPC472548
0.8212	Intermediate Similarity	NPC477905
0.8207	Intermediate Similarity	NPC43241
0.8207	Intermediate Similarity	NPC473081
0.8207	Intermediate Similarity	NPC147880
0.8207	Intermediate Similarity	NPC473758
0.8207	Intermediate Similarity	NPC476094
0.8207	Intermediate Similarity	NPC473613
0.8207	Intermediate Similarity	NPC211137
0.8207	Intermediate Similarity	NPC48017
0.8207	Intermediate Similarity	NPC184747
0.8207	Intermediate Similarity	NPC473060
0.8207	Intermediate Similarity	NPC473085
0.8207	Intermediate Similarity	NPC4341
0.8207	Intermediate Similarity	NPC473440
0.8207	Intermediate Similarity	NPC473112
0.8207	Intermediate Similarity	NPC200592
0.8207	Intermediate Similarity	NPC473109
0.8205	Intermediate Similarity	NPC478073
0.82	Intermediate Similarity	NPC161239
0.82	Intermediate Similarity	NPC31829
0.82	Intermediate Similarity	NPC198455
0.82	Intermediate Similarity	NPC476173

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 NPC140021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	737
0.2-0.3	1601
0.3-0.4	2905
0.4-0.5	2189
0.5-0.6	1165
0.6-0.7	301
0.7-0.8	10
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
0.7697	Intermediate Similarity	NPD7236	Approved
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7239	Suspended
0.7432	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8368	Discontinued
0.7384	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD8407	Phase 2
0.7365	Intermediate Similarity	NPD7799	Discontinued
0.7319	Intermediate Similarity	NPD2629	Approved
0.7248	Intermediate Similarity	NPD7961	Discontinued
0.7234	Intermediate Similarity	NPD7741	Discontinued
0.723	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8360	Approved
0.72	Intermediate Similarity	NPD8361	Approved
0.7184	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6647	Phase 2
0.7143	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8166	Discontinued
0.7115	Intermediate Similarity	NPD4628	Phase 3
0.7102	Intermediate Similarity	NPD8435	Approved
0.707	Intermediate Similarity	NPD6190	Approved
0.7066	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD7058	Phase 2
0.703	Intermediate Similarity	NPD7057	Phase 3
0.6961	Remote Similarity	NPD8485	Approved
0.6903	Remote Similarity	NPD7305	Phase 1
0.6893	Remote Similarity	NPD8150	Discontinued
0.6849	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD37	Approved
0.6835	Remote Similarity	NPD2067	Discontinued
0.6826	Remote Similarity	NPD4965	Approved
0.6826	Remote Similarity	NPD4966	Approved
0.6826	Remote Similarity	NPD4967	Phase 2
0.6821	Remote Similarity	NPD5844	Phase 1
0.6809	Remote Similarity	NPD6858	Approved
0.6809	Remote Similarity	NPD7094	Approved
0.6792	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2066	Phase 3
0.6788	Remote Similarity	NPD5048	Discontinued
0.6786	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7115	Discovery
0.6783	Remote Similarity	NPD4198	Discontinued
0.6781	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7008	Discontinued
0.6763	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6685	Approved
0.6732	Remote Similarity	NPD3764	Approved
0.6728	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6371	Approved
0.6713	Remote Similarity	NPD5951	Approved
0.6713	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7819	Suspended
0.6707	Remote Similarity	NPD5761	Phase 2
0.6707	Remote Similarity	NPD5760	Phase 2
0.6705	Remote Similarity	NPD7685	Pre-registration
0.6705	Remote Similarity	NPD7473	Discontinued
0.669	Remote Similarity	NPD7610	Discontinued
0.6688	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD5125	Phase 3
0.6667	Remote Similarity	NPD5126	Approved
0.6647	Remote Similarity	NPD6234	Discontinued
0.6645	Remote Similarity	NPD5736	Approved
0.6643	Remote Similarity	NPD2182	Approved
0.6643	Remote Similarity	NPD6010	Discontinued
0.6643	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1930	Approved
0.6642	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1929	Approved
0.6627	Remote Similarity	NPD6599	Discontinued
0.6626	Remote Similarity	NPD2532	Approved
0.6626	Remote Similarity	NPD2534	Approved
0.6626	Remote Similarity	NPD2533	Approved
0.661	Remote Similarity	NPD6765	Approved
0.661	Remote Similarity	NPD6764	Approved
0.6607	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD230	Phase 1
0.6596	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5909	Discontinued
0.6588	Remote Similarity	NPD7075	Discontinued
0.6585	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6273	Approved
0.6579	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6085	Phase 2
0.6571	Remote Similarity	NPD7228	Approved
0.6566	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6648	Approved
0.6541	Remote Similarity	NPD6100	Approved
0.6541	Remote Similarity	NPD6099	Approved
0.6538	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD8312	Approved
0.6536	Remote Similarity	NPD8313	Approved
0.6533	Remote Similarity	NPD6637	Approved
0.6532	Remote Similarity	NPD6232	Discontinued
0.6529	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4380	Phase 2
0.6522	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5765	Approved
0.6522	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5494	Approved
0.65	Remote Similarity	NPD5763	Approved
0.65	Remote Similarity	NPD6005	Phase 3
0.65	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6004	Phase 3
0.65	Remote Similarity	NPD5762	Approved
0.65	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6002	Phase 3
0.65	Remote Similarity	NPD7266	Discontinued
0.6497	Remote Similarity	NPD6355	Discontinued
0.6496	Remote Similarity	NPD5344	Discontinued
0.6481	Remote Similarity	NPD4110	Phase 3
0.6481	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2799	Discontinued
0.6477	Remote Similarity	NPD3751	Discontinued
0.6474	Remote Similarity	NPD7715	Approved
0.6474	Remote Similarity	NPD7497	Discontinued
0.6474	Remote Similarity	NPD7714	Approved
0.6471	Remote Similarity	NPD5402	Approved
0.6467	Remote Similarity	NPD6287	Discontinued
0.6467	Remote Similarity	NPD3226	Approved
0.6467	Remote Similarity	NPD4806	Approved
0.6467	Remote Similarity	NPD4807	Approved
0.6464	Remote Similarity	NPD6784	Approved
0.6464	Remote Similarity	NPD6785	Approved
0.6463	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8462	Phase 1
0.6454	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6801	Discontinued
0.6443	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD5306	Approved
0.6443	Remote Similarity	NPD5305	Approved
0.6438	Remote Similarity	NPD2935	Discontinued
0.6424	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7798	Approved
0.6419	Remote Similarity	NPD9545	Approved
0.6418	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD8404	Phase 2
0.6412	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2346	Discontinued
0.6398	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8297	Approved
0.6389	Remote Similarity	NPD6912	Phase 3
0.6384	Remote Similarity	NPD3818	Discontinued
0.6383	Remote Similarity	NPD7700	Phase 2
0.6383	Remote Similarity	NPD7699	Phase 2
0.6383	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3750	Approved
0.638	Remote Similarity	NPD2575	Approved
0.638	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7003	Approved
0.6379	Remote Similarity	NPD7199	Phase 2
0.6375	Remote Similarity	NPD7033	Discontinued
0.6374	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1693	Approved
0.6369	Remote Similarity	NPD8032	Phase 2
0.6369	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6799	Approved
0.6358	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1237	Approved
0.6357	Remote Similarity	NPD164	Approved
0.6354	Remote Similarity	NPD8320	Phase 1
0.6354	Remote Similarity	NPD8319	Approved
0.6353	Remote Similarity	NPD1934	Approved
0.635	Remote Similarity	NPD4225	Approved
0.6343	Remote Similarity	NPD3787	Discontinued
0.6343	Remote Similarity	NPD1088	Approved
0.6337	Remote Similarity	NPD7768	Phase 2
0.6337	Remote Similarity	NPD3882	Suspended
0.6335	Remote Similarity	NPD2438	Suspended
0.6333	Remote Similarity	NPD2932	Approved
0.6333	Remote Similarity	NPD3019	Approved
0.6333	Remote Similarity	NPD6559	Discontinued
0.6333	Remote Similarity	NPD7240	Approved
0.6331	Remote Similarity	NPD1932	Approved
0.6331	Remote Similarity	NPD7028	Phase 2
0.6327	Remote Similarity	NPD3317	Approved
0.6324	Remote Similarity	NPD1989	Approved
0.6316	Remote Similarity	NPD2801	Approved
0.6316	Remote Similarity	NPD1608	Approved
0.6316	Remote Similarity	NPD8455	Phase 2
0.631	Remote Similarity	NPD6534	Approved
0.631	Remote Similarity	NPD6535	Approved
0.6309	Remote Similarity	NPD7009	Phase 2
0.6306	Remote Similarity	NPD3268	Approved
0.6304	Remote Similarity	NPD7640	Approved
0.6304	Remote Similarity	NPD7639	Approved
0.6302	Remote Similarity	NPD7435	Discontinued
0.6301	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2329	Discontinued
0.6294	Remote Similarity	NPD7411	Suspended
0.6291	Remote Similarity	NPD7604	Phase 2

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