NPASS Compound

Structure

NPC471034 OpenBabel07101718322D 23 26 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 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 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 5 1 6 0 0 0 14 19 1 6 0 0 0 14 20 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 1 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	2.024
LogD:	2.342
LogS:	-3.17
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	5.832
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.675
MDCK Permeability:	2.5299805201939307e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.908
30% Bioavailability (F30%):	0.315

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.7
Plasma Protein Binding (PPB):	51.0046501159668%
Volume Distribution (VD):	0.755
Pgp-substrate:	42.34280776977539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.349
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	8.853
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.951
Carcinogencity:	0.849
Eye Corrosion:	0.455
Eye Irritation:	0.359
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC471034

Natural Product ID:	NPC471034
*Common Name:**	PHXVQRJHPRPGAN-XVLAHQNTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PHXVQRJHPRPGAN-XVLAHQNTSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-12-13-5-6-14-19(3)8-4-7-18(2,11-21)15(19)9-16(22)20(14,10-13)17(12)23/h13-16,21-22H,1,4-11H2,2-3H3/t13-,14-,15+,16-,18+,19-,20+/m0/s1
SMILES:	OC[C@@]1(C)CCC[C@@]2([C@@H]1C[C@H](O)[C@]13[C@H]2CC[C@@H](C1)C(=C)C3=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337571
PubChem CID:	71720768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510600]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18161942]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19899773]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22197145]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	whole plants	Vietnam	2009-Aug	PMID[23347584]
NPO22879	Croton tonkinensis	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	45.77	%	PMID[501688]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3950.0	nM	PMID[501688]

☑ 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 NPC471034 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	182
0.1-0.2	1611
0.2-0.3	6304
0.3-0.4	14627
0.4-0.5	7355
0.5-0.6	5570
0.6-0.7	4925
0.7-0.8	1797
0.8-0.85	209
0.85-0.9	70
0.9-0.95	42
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC190704
0.9753	High Similarity	NPC259009
0.9747	High Similarity	NPC471036
0.9747	High Similarity	NPC291320
0.9405	High Similarity	NPC261994
0.9405	High Similarity	NPC470378
0.9405	High Similarity	NPC149761
0.9405	High Similarity	NPC80401
0.9294	High Similarity	NPC299185
0.9294	High Similarity	NPC211403
0.9294	High Similarity	NPC198242
0.9294	High Similarity	NPC476168
0.9277	High Similarity	NPC165895
0.9277	High Similarity	NPC153604
0.9268	High Similarity	NPC102292
0.9186	High Similarity	NPC144739
0.9186	High Similarity	NPC181594
0.9146	High Similarity	NPC146683
0.9136	High Similarity	NPC110780
0.908	High Similarity	NPC261333
0.908	High Similarity	NPC91772
0.908	High Similarity	NPC29247
0.908	High Similarity	NPC289539
0.908	High Similarity	NPC129004
0.908	High Similarity	NPC64006
0.908	High Similarity	NPC215271
0.908	High Similarity	NPC191094
0.908	High Similarity	NPC153775
0.908	High Similarity	NPC104371
0.908	High Similarity	NPC302008
0.908	High Similarity	NPC47853
0.908	High Similarity	NPC111524
0.908	High Similarity	NPC292374
0.908	High Similarity	NPC470385
0.908	High Similarity	NPC101233
0.908	High Similarity	NPC470386
0.9036	High Similarity	NPC76518
0.9024	High Similarity	NPC118800
0.8987	High Similarity	NPC106078
0.8977	High Similarity	NPC231060
0.8977	High Similarity	NPC470232
0.8977	High Similarity	NPC84018
0.8977	High Similarity	NPC138245
0.8953	High Similarity	NPC180849
0.8876	High Similarity	NPC135548
0.8876	High Similarity	NPC264979
0.8876	High Similarity	NPC140242
0.8876	High Similarity	NPC470387
0.8876	High Similarity	NPC329910
0.8864	High Similarity	NPC475118
0.8824	High Similarity	NPC57469
0.8824	High Similarity	NPC174619
0.8795	High Similarity	NPC475726
0.8795	High Similarity	NPC472743
0.8764	High Similarity	NPC470229
0.875	High Similarity	NPC59170
0.875	High Similarity	NPC59350
0.8721	High Similarity	NPC193360
0.8721	High Similarity	NPC471724
0.8721	High Similarity	NPC472739
0.8706	High Similarity	NPC98236
0.8706	High Similarity	NPC269396
0.869	High Similarity	NPC475745
0.869	High Similarity	NPC474482
0.8681	High Similarity	NPC16911
0.8681	High Similarity	NPC78427
0.8681	High Similarity	NPC471038
0.8675	High Similarity	NPC46881
0.8636	High Similarity	NPC278106
0.8636	High Similarity	NPC250753
0.8621	High Similarity	NPC471043
0.8588	High Similarity	NPC292553
0.8587	High Similarity	NPC156324
0.8587	High Similarity	NPC55503
0.8587	High Similarity	NPC127408
0.8587	High Similarity	NPC287676
0.8587	High Similarity	NPC470388
0.8587	High Similarity	NPC291785
0.8556	High Similarity	NPC98639
0.8556	High Similarity	NPC210214
0.8556	High Similarity	NPC29112
0.8539	High Similarity	NPC82138
0.8523	High Similarity	NPC46758
0.8523	High Similarity	NPC100313
0.8523	High Similarity	NPC126993
0.8506	High Similarity	NPC146937
0.8506	High Similarity	NPC471900
0.8495	Intermediate Similarity	NPC52899
0.8495	Intermediate Similarity	NPC289148
0.8495	Intermediate Similarity	NPC71706
0.8495	Intermediate Similarity	NPC471790
0.8495	Intermediate Similarity	NPC46848
0.8495	Intermediate Similarity	NPC163963
0.8488	Intermediate Similarity	NPC472738
0.8478	Intermediate Similarity	NPC474793
0.8471	Intermediate Similarity	NPC74595
0.8471	Intermediate Similarity	NPC474233
0.8471	Intermediate Similarity	NPC264665
0.8462	Intermediate Similarity	NPC200054
0.8462	Intermediate Similarity	NPC13949
0.8462	Intermediate Similarity	NPC29410
0.8434	Intermediate Similarity	NPC164999
0.8427	Intermediate Similarity	NPC470230
0.8427	Intermediate Similarity	NPC272746
0.8409	Intermediate Similarity	NPC213832
0.8409	Intermediate Similarity	NPC57954
0.8404	Intermediate Similarity	NPC148628
0.8404	Intermediate Similarity	NPC286519
0.8404	Intermediate Similarity	NPC309388
0.8404	Intermediate Similarity	NPC88203
0.8404	Intermediate Similarity	NPC475803
0.8404	Intermediate Similarity	NPC272472
0.8404	Intermediate Similarity	NPC246736
0.8404	Intermediate Similarity	NPC304832
0.8404	Intermediate Similarity	NPC214946
0.8404	Intermediate Similarity	NPC275990
0.8404	Intermediate Similarity	NPC76866
0.8391	Intermediate Similarity	NPC472495
0.8391	Intermediate Similarity	NPC4643
0.8391	Intermediate Similarity	NPC472497
0.8375	Intermediate Similarity	NPC308440
0.8375	Intermediate Similarity	NPC472503
0.8372	Intermediate Similarity	NPC264317
0.8372	Intermediate Similarity	NPC294438
0.837	Intermediate Similarity	NPC170978
0.837	Intermediate Similarity	NPC10864
0.8353	Intermediate Similarity	NPC175410
0.8352	Intermediate Similarity	NPC41070
0.8352	Intermediate Similarity	NPC288906
0.8352	Intermediate Similarity	NPC263135
0.8333	Intermediate Similarity	NPC244356
0.8333	Intermediate Similarity	NPC294263
0.8333	Intermediate Similarity	NPC224060
0.8333	Intermediate Similarity	NPC328264
0.8316	Intermediate Similarity	NPC209298
0.8316	Intermediate Similarity	NPC87927
0.8316	Intermediate Similarity	NPC139347
0.8316	Intermediate Similarity	NPC122811
0.8316	Intermediate Similarity	NPC277074
0.8316	Intermediate Similarity	NPC216114
0.8315	Intermediate Similarity	NPC85173
0.8315	Intermediate Similarity	NPC169933
0.8313	Intermediate Similarity	NPC201459
0.8298	Intermediate Similarity	NPC236585
0.8298	Intermediate Similarity	NPC14634
0.8295	Intermediate Similarity	NPC474719
0.8295	Intermediate Similarity	NPC474677
0.8295	Intermediate Similarity	NPC328539
0.8293	Intermediate Similarity	NPC149249
0.8293	Intermediate Similarity	NPC212661
0.8293	Intermediate Similarity	NPC471035
0.8293	Intermediate Similarity	NPC472746
0.828	Intermediate Similarity	NPC162459
0.828	Intermediate Similarity	NPC38296
0.828	Intermediate Similarity	NPC89099
0.828	Intermediate Similarity	NPC38471
0.828	Intermediate Similarity	NPC109059
0.828	Intermediate Similarity	NPC288
0.828	Intermediate Similarity	NPC20479
0.828	Intermediate Similarity	NPC98837
0.828	Intermediate Similarity	NPC28864
0.8276	Intermediate Similarity	NPC12774
0.8276	Intermediate Similarity	NPC72133
0.8276	Intermediate Similarity	NPC2783
0.8276	Intermediate Similarity	NPC34190
0.8261	Intermediate Similarity	NPC234564
0.8242	Intermediate Similarity	NPC196485
0.8242	Intermediate Similarity	NPC471207
0.8242	Intermediate Similarity	NPC209662
0.8242	Intermediate Similarity	NPC245972
0.8242	Intermediate Similarity	NPC280804
0.8242	Intermediate Similarity	NPC111015
0.8235	Intermediate Similarity	NPC477858
0.8235	Intermediate Similarity	NPC145143
0.8229	Intermediate Similarity	NPC13149
0.8229	Intermediate Similarity	NPC98603
0.8229	Intermediate Similarity	NPC84928
0.8222	Intermediate Similarity	NPC233116
0.8222	Intermediate Similarity	NPC475416
0.8222	Intermediate Similarity	NPC131872
0.8214	Intermediate Similarity	NPC472478
0.8202	Intermediate Similarity	NPC186688
0.8202	Intermediate Similarity	NPC119416
0.8191	Intermediate Similarity	NPC293866
0.8191	Intermediate Similarity	NPC267921
0.8182	Intermediate Similarity	NPC475740
0.8182	Intermediate Similarity	NPC264005
0.8182	Intermediate Similarity	NPC33768
0.8182	Intermediate Similarity	NPC269360
0.8182	Intermediate Similarity	NPC298904
0.8172	Intermediate Similarity	NPC108078
0.8172	Intermediate Similarity	NPC253586
0.8161	Intermediate Similarity	NPC470574
0.8161	Intermediate Similarity	NPC201655
0.8152	Intermediate Similarity	NPC266431
0.8152	Intermediate Similarity	NPC472485
0.8152	Intermediate Similarity	NPC271195
0.8144	Intermediate Similarity	NPC4115
0.8144	Intermediate Similarity	NPC12823
0.8144	Intermediate Similarity	NPC200957

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 NPC471034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2081
0.2-0.3	4220
0.3-0.4	1844
0.4-0.5	419
0.5-0.6	138
0.6-0.7	178
0.7-0.8	92
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD4788	Approved
0.8276	Intermediate Similarity	NPD3618	Phase 1
0.8222	Intermediate Similarity	NPD6079	Approved
0.8202	Intermediate Similarity	NPD5328	Approved
0.8049	Intermediate Similarity	NPD3703	Phase 2
0.8046	Intermediate Similarity	NPD4786	Approved
0.8023	Intermediate Similarity	NPD3667	Approved
0.7935	Intermediate Similarity	NPD4202	Approved
0.7901	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5222	Approved
0.7872	Intermediate Similarity	NPD5221	Approved
0.7841	Intermediate Similarity	NPD3665	Phase 1
0.7841	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD3666	Approved
0.7789	Intermediate Similarity	NPD5173	Approved
0.7765	Intermediate Similarity	NPD6697	Approved
0.7765	Intermediate Similarity	NPD6114	Approved
0.7765	Intermediate Similarity	NPD6118	Approved
0.7765	Intermediate Similarity	NPD6115	Approved
0.7684	Intermediate Similarity	NPD4697	Phase 3
0.7667	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4634	Approved
0.7634	Intermediate Similarity	NPD8034	Phase 2
0.7634	Intermediate Similarity	NPD7515	Phase 2
0.7634	Intermediate Similarity	NPD8035	Phase 2
0.7629	Intermediate Similarity	NPD5286	Approved
0.7629	Intermediate Similarity	NPD4696	Approved
0.7629	Intermediate Similarity	NPD5285	Approved
0.7604	Intermediate Similarity	NPD4755	Approved
0.7551	Intermediate Similarity	NPD5223	Approved
0.7529	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5226	Approved
0.7475	Intermediate Similarity	NPD5224	Approved
0.7475	Intermediate Similarity	NPD4633	Approved
0.7475	Intermediate Similarity	NPD5211	Phase 2
0.7475	Intermediate Similarity	NPD5225	Approved
0.7473	Intermediate Similarity	NPD5279	Phase 3
0.7449	Intermediate Similarity	NPD4700	Approved
0.7442	Intermediate Similarity	NPD6116	Phase 1
0.7439	Intermediate Similarity	NPD3698	Phase 2
0.7419	Intermediate Similarity	NPD4753	Phase 2
0.7416	Intermediate Similarity	NPD4223	Phase 3
0.7416	Intermediate Similarity	NPD4221	Approved
0.74	Intermediate Similarity	NPD5175	Approved
0.74	Intermediate Similarity	NPD5174	Approved
0.7386	Intermediate Similarity	NPD7525	Registered
0.7375	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4789	Approved
0.7349	Intermediate Similarity	NPD4245	Approved
0.7349	Intermediate Similarity	NPD4244	Approved
0.7347	Intermediate Similarity	NPD7638	Approved
0.7327	Intermediate Similarity	NPD5141	Approved
0.7317	Intermediate Similarity	NPD5360	Phase 3
0.7317	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7253	Intermediate Similarity	NPD4197	Approved
0.7253	Intermediate Similarity	NPD3668	Phase 3
0.7228	Intermediate Similarity	NPD4754	Approved
0.7216	Intermediate Similarity	NPD4629	Approved
0.7216	Intermediate Similarity	NPD5210	Approved
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.7184	Intermediate Similarity	NPD5697	Approved
0.7174	Intermediate Similarity	NPD5329	Approved
0.7159	Intermediate Similarity	NPD3671	Phase 1
0.7159	Intermediate Similarity	NPD3617	Approved
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.7115	Intermediate Similarity	NPD4729	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7115	Intermediate Similarity	NPD4730	Approved
0.7115	Intermediate Similarity	NPD5128	Approved
0.7115	Intermediate Similarity	NPD5168	Approved
0.7103	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD5205	Approved
0.7097	Intermediate Similarity	NPD4693	Phase 3
0.7097	Intermediate Similarity	NPD4690	Approved
0.7097	Intermediate Similarity	NPD5690	Phase 2
0.7097	Intermediate Similarity	NPD4688	Approved
0.7097	Intermediate Similarity	NPD4689	Approved
0.7097	Intermediate Similarity	NPD4138	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD4768	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD4767	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7073	Intermediate Similarity	NPD4224	Phase 2
0.7071	Intermediate Similarity	NPD7902	Approved
0.7059	Intermediate Similarity	NPD4758	Discontinued
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.7048	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6054	Approved
0.7027	Intermediate Similarity	NPD6319	Approved
0.7019	Intermediate Similarity	NPD5701	Approved
0.7011	Intermediate Similarity	NPD7339	Approved
0.7011	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD4695	Discontinued
0.6981	Remote Similarity	NPD5169	Approved
0.6981	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5248	Approved
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD5250	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6981	Remote Similarity	NPD5247	Approved
0.6981	Remote Similarity	NPD5135	Approved
0.6981	Remote Similarity	NPD5251	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.6981	Remote Similarity	NPD5249	Phase 3
0.6964	Remote Similarity	NPD6016	Approved
0.6964	Remote Similarity	NPD6015	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6947	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6650	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6916	Remote Similarity	NPD5127	Approved
0.6916	Remote Similarity	NPD5215	Approved
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD5216	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD5217	Approved
0.6916	Remote Similarity	NPD6649	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6915	Remote Similarity	NPD5280	Approved
0.6915	Remote Similarity	NPD7334	Approved
0.6915	Remote Similarity	NPD6409	Approved
0.6915	Remote Similarity	NPD6684	Approved
0.6915	Remote Similarity	NPD7146	Approved
0.6915	Remote Similarity	NPD7521	Approved
0.6915	Remote Similarity	NPD5330	Approved
0.6915	Remote Similarity	NPD4694	Approved
0.6909	Remote Similarity	NPD6009	Approved
0.6909	Remote Similarity	NPD7115	Discovery
0.6903	Remote Similarity	NPD6370	Approved
0.6903	Remote Similarity	NPD5988	Approved
0.69	Remote Similarity	NPD6083	Phase 2
0.69	Remote Similarity	NPD6084	Phase 2
0.6889	Remote Similarity	NPD7645	Phase 2
0.6889	Remote Similarity	NPD4195	Approved
0.6887	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.6875	Remote Similarity	NPD6059	Approved
0.6852	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6796	Remote Similarity	NPD7632	Discontinued
0.6783	Remote Similarity	NPD7492	Approved
0.6771	Remote Similarity	NPD6903	Approved
0.6771	Remote Similarity	NPD6672	Approved
0.6771	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD7900	Approved
0.6768	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6008	Approved
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7736	Approved
0.6744	Remote Similarity	NPD4747	Approved
0.6744	Remote Similarity	NPD4691	Approved
0.6739	Remote Similarity	NPD4692	Approved
0.6739	Remote Similarity	NPD4139	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6727	Remote Similarity	NPD5167	Approved
0.6724	Remote Similarity	NPD6616	Approved
0.67	Remote Similarity	NPD5695	Phase 3
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6081	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6637	Remote Similarity	NPD4522	Approved
0.6636	Remote Similarity	NPD8133	Approved
0.6636	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4137	Phase 3
0.6607	Remote Similarity	NPD6317	Approved
0.6593	Remote Similarity	NPD5364	Discontinued
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6552	Remote Similarity	NPD7604	Phase 2
0.6549	Remote Similarity	NPD6335	Approved
0.6549	Remote Similarity	NPD6313	Approved
0.6549	Remote Similarity	NPD6314	Approved
0.6535	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8293	Discontinued
0.6522	Remote Similarity	NPD6929	Approved
0.6517	Remote Similarity	NPD4058	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