NPASS Compound

Structure

NPC106078 OpenBabel07101719512D 22 25 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 -0.6397 -1.0707 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 -0.0108 -0.7200 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 2 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 -0.6182 0.3693 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 1 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 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 4 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 5 1 1 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 22 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:	302.22
Volume:	332.558
LogP:	3.032
LogD:	2.979
LogS:	-4.156
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	5.577
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.765
MDCK Permeability:	1.5703046301496215e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	89.53733825683594%
Volume Distribution (VD):	0.831
Pgp-substrate:	5.83777379989624%

ADMET: Metabolism

CYP1A2-inhibitor:	0.218
CYP1A2-substrate:	0.322
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.71
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	6.497
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.54
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.935
Carcinogencity:	0.477
Eye Corrosion:	0.416
Eye Irritation:	0.618
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC106078

Natural Product ID:	NPC106078
*Common Name:**	NYWYTVLBFMICLI-SLBIIXIFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NYWYTVLBFMICLI-SLBIIXIFSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13-14-5-6-16-19(3)9-4-8-18(2,12-21)15(19)7-10-20(16,11-14)17(13)22/h14-16,21H,1,4-12H2,2-3H3/t14-,15-,16+,18-,19-,20-/m1/s1
SMILES:	OC[C@@]1(C)CCC[C@@]2([C@@H]1CC[C@]13[C@H]2CC[C@H](C1)C(=C)C3=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253558
PubChem CID:	44445572
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
EC50	4
Others	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	6.52	ug.mL-1	PMID[497412]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	4.31	ug.mL-1	PMID[497412]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	1.47	ug.mL-1	PMID[497412]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1.31	ug.mL-1	PMID[497412]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	17.96	%	PMID[497413]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	29.89	%	PMID[497413]

☑ 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 NPC106078 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	153
0.1-0.2	1487
0.2-0.3	7409
0.3-0.4	15582
0.4-0.5	6189
0.5-0.6	6299
0.6-0.7	3766
0.7-0.8	1536
0.8-0.85	211
0.85-0.9	51
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC175410
0.9221	High Similarity	NPC118800
0.9221	High Similarity	NPC471036
0.9221	High Similarity	NPC291320
0.92	High Similarity	NPC201459
0.9189	High Similarity	NPC212661
0.9189	High Similarity	NPC471035
0.9103	High Similarity	NPC146683
0.9079	High Similarity	NPC472478
0.8987	High Similarity	NPC471034
0.8987	High Similarity	NPC76518
0.8987	High Similarity	NPC190704
0.8987	High Similarity	NPC102292
0.8961	High Similarity	NPC474484
0.8961	High Similarity	NPC103754
0.8947	High Similarity	NPC472490
0.8933	High Similarity	NPC149249
0.8933	High Similarity	NPC476811
0.8846	High Similarity	NPC110780
0.8846	High Similarity	NPC145143
0.8846	High Similarity	NPC477858
0.8846	High Similarity	NPC46881
0.8816	High Similarity	NPC476810
0.8765	High Similarity	NPC153604
0.8765	High Similarity	NPC174619
0.8765	High Similarity	NPC93778
0.8765	High Similarity	NPC259009
0.8765	High Similarity	NPC165895
0.8734	High Similarity	NPC472498
0.8734	High Similarity	NPC475726
0.8734	High Similarity	NPC472743
0.8701	High Similarity	NPC471475
0.8701	High Similarity	NPC476812
0.8659	High Similarity	NPC472739
0.8649	High Similarity	NPC330659
0.8649	High Similarity	NPC244708
0.8649	High Similarity	NPC161187
0.8642	High Similarity	NPC269396
0.8642	High Similarity	NPC98236
0.8625	High Similarity	NPC214043
0.8625	High Similarity	NPC474482
0.8625	High Similarity	NPC237712
0.8625	High Similarity	NPC475745
0.8625	High Similarity	NPC85774
0.8625	High Similarity	NPC474233
0.8608	High Similarity	NPC170985
0.859	High Similarity	NPC164999
0.8519	High Similarity	NPC469948
0.8519	High Similarity	NPC201655
0.8519	High Similarity	NPC292553
0.85	High Similarity	NPC245866
0.85	High Similarity	NPC472740
0.8481	Intermediate Similarity	NPC164210
0.8462	Intermediate Similarity	NPC215843
0.8462	Intermediate Similarity	NPC192744
0.8452	Intermediate Similarity	NPC180849
0.8452	Intermediate Similarity	NPC470378
0.8452	Intermediate Similarity	NPC126993
0.8452	Intermediate Similarity	NPC149761
0.8452	Intermediate Similarity	NPC80401
0.8452	Intermediate Similarity	NPC261994
0.8442	Intermediate Similarity	NPC66105
0.8434	Intermediate Similarity	NPC56413
0.8415	Intermediate Similarity	NPC472738
0.8415	Intermediate Similarity	NPC31564
0.8415	Intermediate Similarity	NPC474732
0.8415	Intermediate Similarity	NPC474733
0.8415	Intermediate Similarity	NPC474778
0.8415	Intermediate Similarity	NPC145879
0.8415	Intermediate Similarity	NPC70661
0.8395	Intermediate Similarity	NPC74595
0.8395	Intermediate Similarity	NPC263974
0.8395	Intermediate Similarity	NPC82902
0.8395	Intermediate Similarity	NPC473246
0.8395	Intermediate Similarity	NPC321187
0.8395	Intermediate Similarity	NPC161423
0.8395	Intermediate Similarity	NPC58841
0.8395	Intermediate Similarity	NPC227064
0.8395	Intermediate Similarity	NPC329043
0.8395	Intermediate Similarity	NPC59453
0.8395	Intermediate Similarity	NPC264665
0.8395	Intermediate Similarity	NPC221758
0.8375	Intermediate Similarity	NPC151519
0.8354	Intermediate Similarity	NPC2482
0.8353	Intermediate Similarity	NPC250753
0.8353	Intermediate Similarity	NPC476168
0.8353	Intermediate Similarity	NPC272746
0.8353	Intermediate Similarity	NPC198242
0.8353	Intermediate Similarity	NPC278106
0.8353	Intermediate Similarity	NPC211403
0.8353	Intermediate Similarity	NPC299185
0.8333	Intermediate Similarity	NPC103734
0.8313	Intermediate Similarity	NPC472495
0.8313	Intermediate Similarity	NPC4643
0.8313	Intermediate Similarity	NPC472497
0.8313	Intermediate Similarity	NPC58063
0.8313	Intermediate Similarity	NPC57469
0.8313	Intermediate Similarity	NPC475740
0.8312	Intermediate Similarity	NPC246445
0.8293	Intermediate Similarity	NPC474218
0.8293	Intermediate Similarity	NPC264317
0.8293	Intermediate Similarity	NPC294438
0.8293	Intermediate Similarity	NPC471224
0.8272	Intermediate Similarity	NPC471037
0.8256	Intermediate Similarity	NPC59350
0.8256	Intermediate Similarity	NPC294263
0.8256	Intermediate Similarity	NPC181594
0.8256	Intermediate Similarity	NPC144739
0.8256	Intermediate Similarity	NPC59170
0.8256	Intermediate Similarity	NPC82138
0.825	Intermediate Similarity	NPC328264
0.825	Intermediate Similarity	NPC121984
0.825	Intermediate Similarity	NPC3915
0.8243	Intermediate Similarity	NPC475952
0.8235	Intermediate Similarity	NPC85173
0.8214	Intermediate Similarity	NPC474719
0.8214	Intermediate Similarity	NPC474677
0.8214	Intermediate Similarity	NPC471724
0.8214	Intermediate Similarity	NPC328539
0.8214	Intermediate Similarity	NPC193360
0.8205	Intermediate Similarity	NPC472746
0.8205	Intermediate Similarity	NPC68828
0.8194	Intermediate Similarity	NPC476737
0.8194	Intermediate Similarity	NPC27243
0.8193	Intermediate Similarity	NPC34190
0.8193	Intermediate Similarity	NPC473168
0.8193	Intermediate Similarity	NPC327115
0.8193	Intermediate Similarity	NPC12774
0.8193	Intermediate Similarity	NPC2783
0.8193	Intermediate Similarity	NPC51014
0.8193	Intermediate Similarity	NPC72133
0.8193	Intermediate Similarity	NPC469994
0.8193	Intermediate Similarity	NPC80590
0.8171	Intermediate Similarity	NPC472265
0.8161	Intermediate Similarity	NPC261333
0.8161	Intermediate Similarity	NPC470386
0.8161	Intermediate Similarity	NPC292374
0.8161	Intermediate Similarity	NPC215271
0.8161	Intermediate Similarity	NPC64006
0.8161	Intermediate Similarity	NPC29247
0.8161	Intermediate Similarity	NPC104371
0.8161	Intermediate Similarity	NPC129004
0.8161	Intermediate Similarity	NPC101233
0.8161	Intermediate Similarity	NPC289539
0.8161	Intermediate Similarity	NPC191094
0.8161	Intermediate Similarity	NPC153775
0.8161	Intermediate Similarity	NPC470385
0.8161	Intermediate Similarity	NPC91772
0.8161	Intermediate Similarity	NPC47853
0.8161	Intermediate Similarity	NPC302008
0.8161	Intermediate Similarity	NPC111524
0.8158	Intermediate Similarity	NPC279241
0.8148	Intermediate Similarity	NPC310989
0.8148	Intermediate Similarity	NPC193347
0.8133	Intermediate Similarity	NPC476731
0.8133	Intermediate Similarity	NPC91369
0.8118	Intermediate Similarity	NPC326627
0.8118	Intermediate Similarity	NPC472475
0.8118	Intermediate Similarity	NPC310010
0.8118	Intermediate Similarity	NPC186688
0.8118	Intermediate Similarity	NPC26959
0.8118	Intermediate Similarity	NPC309603
0.8118	Intermediate Similarity	NPC1015
0.8118	Intermediate Similarity	NPC31985
0.8118	Intermediate Similarity	NPC477943
0.8118	Intermediate Similarity	NPC472477
0.8118	Intermediate Similarity	NPC119416
0.8118	Intermediate Similarity	NPC473999
0.8118	Intermediate Similarity	NPC268406
0.8101	Intermediate Similarity	NPC82635
0.8101	Intermediate Similarity	NPC63020
0.8095	Intermediate Similarity	NPC269360
0.8095	Intermediate Similarity	NPC90652
0.8095	Intermediate Similarity	NPC136548
0.8095	Intermediate Similarity	NPC317590
0.8095	Intermediate Similarity	NPC264005
0.8095	Intermediate Similarity	NPC33768
0.8095	Intermediate Similarity	NPC96496
0.8095	Intermediate Similarity	NPC134197
0.8077	Intermediate Similarity	NPC20466
0.8072	Intermediate Similarity	NPC474083
0.8072	Intermediate Similarity	NPC470574
0.8072	Intermediate Similarity	NPC29447
0.8068	Intermediate Similarity	NPC476174
0.8068	Intermediate Similarity	NPC470232
0.8068	Intermediate Similarity	NPC210214
0.8068	Intermediate Similarity	NPC231060
0.8068	Intermediate Similarity	NPC98639
0.8068	Intermediate Similarity	NPC138245
0.8068	Intermediate Similarity	NPC29112
0.8068	Intermediate Similarity	NPC84018
0.8052	Intermediate Similarity	NPC199316
0.8052	Intermediate Similarity	NPC102313
0.8052	Intermediate Similarity	NPC159497
0.8049	Intermediate Similarity	NPC307258
0.8046	Intermediate Similarity	NPC12722
0.8046	Intermediate Similarity	NPC474736
0.8046	Intermediate Similarity	NPC474807
0.8026	Intermediate Similarity	NPC151018
0.8026	Intermediate Similarity	NPC473267

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 NPC106078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1922
0.2-0.3	4340
0.3-0.4	1876
0.4-0.5	439
0.5-0.6	146
0.6-0.7	163
0.7-0.8	93
0.8-0.85	21
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD4788	Approved
0.8395	Intermediate Similarity	NPD3665	Phase 1
0.8395	Intermediate Similarity	NPD3133	Approved
0.8395	Intermediate Similarity	NPD3666	Approved
0.8395	Intermediate Similarity	NPD4786	Approved
0.8375	Intermediate Similarity	NPD3667	Approved
0.8293	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3618	Phase 1
0.8148	Intermediate Similarity	NPD4221	Approved
0.8148	Intermediate Similarity	NPD4223	Phase 3
0.814	Intermediate Similarity	NPD6079	Approved
0.8133	Intermediate Similarity	NPD4789	Approved
0.8118	Intermediate Similarity	NPD4753	Phase 2
0.8118	Intermediate Similarity	NPD5328	Approved
0.8026	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3698	Phase 2
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD5279	Phase 3
0.7952	Intermediate Similarity	NPD4197	Approved
0.7895	Intermediate Similarity	NPD4245	Approved
0.7895	Intermediate Similarity	NPD4244	Approved
0.7875	Intermediate Similarity	NPD3617	Approved
0.7865	Intermediate Similarity	NPD5210	Approved
0.7865	Intermediate Similarity	NPD4629	Approved
0.7857	Intermediate Similarity	NPD5329	Approved
0.7841	Intermediate Similarity	NPD4202	Approved
0.7838	Intermediate Similarity	NPD4224	Phase 2
0.7778	Intermediate Similarity	NPD5222	Approved
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5221	Approved
0.7765	Intermediate Similarity	NPD5205	Approved
0.7765	Intermediate Similarity	NPD4138	Approved
0.7765	Intermediate Similarity	NPD4690	Approved
0.7765	Intermediate Similarity	NPD4688	Approved
0.7765	Intermediate Similarity	NPD4693	Phase 3
0.7765	Intermediate Similarity	NPD4689	Approved
0.7765	Intermediate Similarity	NPD5690	Phase 2
0.7692	Intermediate Similarity	NPD5173	Approved
0.7683	Intermediate Similarity	NPD4695	Discontinued
0.7632	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5360	Phase 3
0.7595	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4697	Phase 3
0.7561	Intermediate Similarity	NPD4195	Approved
0.7558	Intermediate Similarity	NPD5280	Approved
0.7558	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4694	Approved
0.7529	Intermediate Similarity	NPD3668	Phase 3
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.7528	Intermediate Similarity	NPD8034	Phase 2
0.7528	Intermediate Similarity	NPD8035	Phase 2
0.7527	Intermediate Similarity	NPD4696	Approved
0.7527	Intermediate Similarity	NPD5285	Approved
0.7527	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD3703	Phase 2
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7447	Intermediate Similarity	NPD5223	Approved
0.7444	Intermediate Similarity	NPD6399	Phase 3
0.7436	Intermediate Similarity	NPD4747	Approved
0.7436	Intermediate Similarity	NPD4691	Approved
0.7407	Intermediate Similarity	NPD6117	Approved
0.7386	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5737	Approved
0.7386	Intermediate Similarity	NPD6672	Approved
0.7381	Intermediate Similarity	NPD4692	Approved
0.7381	Intermediate Similarity	NPD4139	Approved
0.7368	Intermediate Similarity	NPD4633	Approved
0.7368	Intermediate Similarity	NPD5224	Approved
0.7368	Intermediate Similarity	NPD5225	Approved
0.7368	Intermediate Similarity	NPD5211	Phase 2
0.7368	Intermediate Similarity	NPD5226	Approved
0.7356	Intermediate Similarity	NPD6684	Approved
0.7356	Intermediate Similarity	NPD4623	Approved
0.7356	Intermediate Similarity	NPD6409	Approved
0.7356	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD5330	Approved
0.7356	Intermediate Similarity	NPD7521	Approved
0.7356	Intermediate Similarity	NPD7334	Approved
0.7356	Intermediate Similarity	NPD4519	Discontinued
0.7342	Intermediate Similarity	NPD6081	Approved
0.7342	Intermediate Similarity	NPD4758	Discontinued
0.734	Intermediate Similarity	NPD4700	Approved
0.7317	Intermediate Similarity	NPD6116	Phase 1
0.7308	Intermediate Similarity	NPD4137	Phase 3
0.7292	Intermediate Similarity	NPD5174	Approved
0.7292	Intermediate Similarity	NPD5175	Approved
0.7284	Intermediate Similarity	NPD7339	Approved
0.7284	Intermediate Similarity	NPD6942	Approved
0.7283	Intermediate Similarity	NPD5695	Phase 3
0.7262	Intermediate Similarity	NPD7525	Registered
0.7234	Intermediate Similarity	NPD5696	Approved
0.7229	Intermediate Similarity	NPD6697	Approved
0.7229	Intermediate Similarity	NPD3671	Phase 1
0.7229	Intermediate Similarity	NPD6118	Approved
0.7229	Intermediate Similarity	NPD6115	Approved
0.7229	Intermediate Similarity	NPD6114	Approved
0.7216	Intermediate Similarity	NPD5141	Approved
0.7195	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6903	Approved
0.7174	Intermediate Similarity	NPD7748	Approved
0.716	Intermediate Similarity	NPD4058	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7113	Intermediate Similarity	NPD4754	Approved
0.7073	Intermediate Similarity	NPD3702	Approved
0.7071	Intermediate Similarity	NPD5697	Approved
0.7033	Intermediate Similarity	NPD4096	Approved
0.7	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD5208	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD4729	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD4730	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD5168	Approved
0.697	Remote Similarity	NPD7128	Approved
0.697	Remote Similarity	NPD4767	Approved
0.697	Remote Similarity	NPD4768	Approved
0.697	Remote Similarity	NPD6402	Approved
0.697	Remote Similarity	NPD6675	Approved
0.697	Remote Similarity	NPD5739	Approved
0.6966	Remote Similarity	NPD6098	Approved
0.6962	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5733	Approved
0.6951	Remote Similarity	NPD6924	Approved
0.6951	Remote Similarity	NPD4687	Approved
0.6951	Remote Similarity	NPD6926	Approved
0.6947	Remote Similarity	NPD7902	Approved
0.6931	Remote Similarity	NPD6012	Approved
0.6931	Remote Similarity	NPD6013	Approved
0.6931	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6673	Approved
0.6923	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD6080	Approved
0.6923	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5276	Approved
0.6914	Remote Similarity	NPD4243	Approved
0.6914	Remote Similarity	NPD5777	Approved
0.69	Remote Similarity	NPD5701	Approved
0.6897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD7638	Approved
0.6863	Remote Similarity	NPD5169	Approved
0.6863	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6883	Approved
0.6863	Remote Similarity	NPD5251	Approved
0.6863	Remote Similarity	NPD5248	Approved
0.6863	Remote Similarity	NPD5250	Approved
0.6863	Remote Similarity	NPD5247	Approved
0.6863	Remote Similarity	NPD5135	Approved
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD5249	Phase 3
0.6863	Remote Similarity	NPD7290	Approved
0.6863	Remote Similarity	NPD4634	Approved
0.6837	Remote Similarity	NPD5091	Approved
0.6832	Remote Similarity	NPD7320	Approved
0.6824	Remote Similarity	NPD5364	Discontinued
0.6813	Remote Similarity	NPD4518	Approved
0.6804	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD5216	Approved
0.6796	Remote Similarity	NPD5217	Approved
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD5215	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD5127	Approved
0.6796	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6786	Remote Similarity	NPD6933	Approved
0.6774	Remote Similarity	NPD5693	Phase 1
0.6765	Remote Similarity	NPD6373	Approved
0.6765	Remote Similarity	NPD6372	Approved
0.6747	Remote Similarity	NPD4784	Approved
0.6747	Remote Similarity	NPD4785	Approved
0.6744	Remote Similarity	NPD7645	Phase 2
0.6737	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6412	Phase 2
0.6731	Remote Similarity	NPD6882	Approved
0.6731	Remote Similarity	NPD8297	Approved
0.6703	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD5275	Approved
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD4190	Phase 3
0.6635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6001	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6628	Remote Similarity	NPD5784	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