NPASS Compound

Structure

NPC471475 OpenBabel07101718242D 25 28 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 -1.9386 -4.5157 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 -1.4257 -3.6573 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 -0.4258 -3.6723 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 -1.9127 -2.7839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 15 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 6 1 1 0 0 0 17 20 1 6 0 0 0 17 21 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 3 1 6 0 0 0 21 4 1 6 0 0 0 22 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	373.304
LogP:	3.814
LogD:	3.401
LogS:	-4.774
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	5.555
Fsp3:	0.818
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:	-4.882
MDCK Permeability:	2.215646418335382e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.392
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.158
Plasma Protein Binding (PPB):	84.05249786376953%
Volume Distribution (VD):	0.992
Pgp-substrate:	16.494590759277344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.196
CYP1A2-substrate:	0.243
CYP2C19-inhibitor:	0.155
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	2.528
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.467
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.35
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.937
Carcinogencity:	0.451
Eye Corrosion:	0.391
Eye Irritation:	0.485
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC471475

Natural Product ID:	NPC471475
*Common Name:**	PCIAHXQFOUORIJ-UQYSYHQNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PCIAHXQFOUORIJ-UQYSYHQNSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-14-16-6-7-18-21(4)10-5-9-20(3,13-25-15(2)23)17(21)8-11-22(18,12-16)19(14)24/h16-18H,1,5-13H2,2-4H3/t16-,17-,18+,20-,21-,22-/m1/s1
SMILES:	CC(=O)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:	CHEMBL252111
PubChem CID:	44445570
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
IC50	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	=	6.56	ug.mL-1	PMID[508922]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	6.11	ug.mL-1	PMID[508922]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	3.75	ug.mL-1	PMID[508922]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	2.84	ug.mL-1	PMID[508922]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	240.0	nM	PMID[508923]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	130.0	nM	PMID[508923]

☑ 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 NPC471475 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	183
0.1-0.2	1650
0.2-0.3	8068
0.3-0.4	14707
0.4-0.5	6067
0.5-0.6	6441
0.6-0.7	4128
0.7-0.8	1325
0.8-0.85	102
0.85-0.9	21
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9178	High Similarity	NPC279241
0.9125	High Similarity	NPC471042
0.9079	High Similarity	NPC63020
0.8947	High Similarity	NPC212661
0.8947	High Similarity	NPC471035
0.8861	High Similarity	NPC476458
0.8861	High Similarity	NPC258153
0.8795	High Similarity	NPC471043
0.875	High Similarity	NPC170862
0.875	High Similarity	NPC471037
0.8701	High Similarity	NPC106078
0.8642	High Similarity	NPC475509
0.8608	High Similarity	NPC170038
0.8588	High Similarity	NPC470230
0.8537	High Similarity	NPC470223
0.8537	High Similarity	NPC98270
0.8519	High Similarity	NPC472740
0.8488	Intermediate Similarity	NPC294263
0.8488	Intermediate Similarity	NPC475700
0.8481	Intermediate Similarity	NPC192744
0.8481	Intermediate Similarity	NPC118987
0.8462	Intermediate Similarity	NPC66105
0.8452	Intermediate Similarity	NPC56413
0.8434	Intermediate Similarity	NPC195640
0.8434	Intermediate Similarity	NPC472505
0.8421	Intermediate Similarity	NPC244708
0.8421	Intermediate Similarity	NPC330659
0.8421	Intermediate Similarity	NPC161187
0.8415	Intermediate Similarity	NPC263974
0.8395	Intermediate Similarity	NPC100297
0.8391	Intermediate Similarity	NPC47853
0.8372	Intermediate Similarity	NPC250753
0.8372	Intermediate Similarity	NPC218301
0.8354	Intermediate Similarity	NPC476810
0.8333	Intermediate Similarity	NPC246445
0.8313	Intermediate Similarity	NPC323765
0.8313	Intermediate Similarity	NPC474971
0.8313	Intermediate Similarity	NPC201655
0.8295	Intermediate Similarity	NPC470229
0.8295	Intermediate Similarity	NPC98639
0.8295	Intermediate Similarity	NPC210214
0.8295	Intermediate Similarity	NPC280877
0.8293	Intermediate Similarity	NPC175410
0.8293	Intermediate Similarity	NPC245866
0.825	Intermediate Similarity	NPC201459
0.8235	Intermediate Similarity	NPC4309
0.8235	Intermediate Similarity	NPC28227
0.8228	Intermediate Similarity	NPC472300
0.8228	Intermediate Similarity	NPC68828
0.8228	Intermediate Similarity	NPC475932
0.8214	Intermediate Similarity	NPC264127
0.8214	Intermediate Similarity	NPC12774
0.8214	Intermediate Similarity	NPC70661
0.8202	Intermediate Similarity	NPC200054
0.8202	Intermediate Similarity	NPC329910
0.8202	Intermediate Similarity	NPC29410
0.8193	Intermediate Similarity	NPC312660
0.8182	Intermediate Similarity	NPC475118
0.8171	Intermediate Similarity	NPC142683
0.8171	Intermediate Similarity	NPC327969
0.8171	Intermediate Similarity	NPC476935
0.8171	Intermediate Similarity	NPC321289
0.8171	Intermediate Similarity	NPC170985
0.8148	Intermediate Similarity	NPC267517
0.814	Intermediate Similarity	NPC11611
0.814	Intermediate Similarity	NPC474570
0.8118	Intermediate Similarity	NPC134197
0.8118	Intermediate Similarity	NPC33768
0.8101	Intermediate Similarity	NPC20466
0.8101	Intermediate Similarity	NPC476601
0.8101	Intermediate Similarity	NPC92489
0.8095	Intermediate Similarity	NPC29447
0.8095	Intermediate Similarity	NPC264317
0.8095	Intermediate Similarity	NPC76518
0.8095	Intermediate Similarity	NPC294438
0.809	Intermediate Similarity	NPC470232
0.8077	Intermediate Similarity	NPC159497
0.8072	Intermediate Similarity	NPC291320
0.8072	Intermediate Similarity	NPC471036
0.8072	Intermediate Similarity	NPC118800
0.8049	Intermediate Similarity	NPC103754
0.8049	Intermediate Similarity	NPC232625
0.8049	Intermediate Similarity	NPC474484
0.8049	Intermediate Similarity	NPC474955
0.8049	Intermediate Similarity	NPC147066
0.8046	Intermediate Similarity	NPC475965
0.8046	Intermediate Similarity	NPC474842
0.8026	Intermediate Similarity	NPC477857
0.8025	Intermediate Similarity	NPC47808
0.8025	Intermediate Similarity	NPC305835
0.8023	Intermediate Similarity	NPC97884
0.8023	Intermediate Similarity	NPC474719
0.8023	Intermediate Similarity	NPC472220
0.8023	Intermediate Similarity	NPC474845
0.8023	Intermediate Similarity	NPC255176
0.8022	Intermediate Similarity	NPC28864
0.8022	Intermediate Similarity	NPC162459
0.8022	Intermediate Similarity	NPC16911
0.8022	Intermediate Similarity	NPC471038
0.8022	Intermediate Similarity	NPC38471
0.8022	Intermediate Similarity	NPC98837
0.8022	Intermediate Similarity	NPC78427
0.8022	Intermediate Similarity	NPC20479
0.8022	Intermediate Similarity	NPC38296
0.8	Intermediate Similarity	NPC2783
0.8	Intermediate Similarity	NPC13949
0.8	Intermediate Similarity	NPC104568
0.8	Intermediate Similarity	NPC58052
0.8	Intermediate Similarity	NPC149249
0.8	Intermediate Similarity	NPC80590
0.8	Intermediate Similarity	NPC238227
0.8	Intermediate Similarity	NPC111684
0.7978	Intermediate Similarity	NPC41649
0.7978	Intermediate Similarity	NPC470385
0.7978	Intermediate Similarity	NPC470386
0.7976	Intermediate Similarity	NPC146683
0.7976	Intermediate Similarity	NPC320801
0.7976	Intermediate Similarity	NPC100391
0.7976	Intermediate Similarity	NPC109512
0.7955	Intermediate Similarity	NPC160506
0.7955	Intermediate Similarity	NPC475416
0.7955	Intermediate Similarity	NPC198242
0.7955	Intermediate Similarity	NPC211403
0.7955	Intermediate Similarity	NPC471901
0.7952	Intermediate Similarity	NPC145143
0.7952	Intermediate Similarity	NPC240302
0.7952	Intermediate Similarity	NPC477858
0.7952	Intermediate Similarity	NPC320514
0.7952	Intermediate Similarity	NPC226988
0.7949	Intermediate Similarity	NPC36310
0.7935	Intermediate Similarity	NPC287676
0.7935	Intermediate Similarity	NPC293866
0.7931	Intermediate Similarity	NPC469546
0.7931	Intermediate Similarity	NPC285982
0.7931	Intermediate Similarity	NPC305039
0.7927	Intermediate Similarity	NPC474956
0.7927	Intermediate Similarity	NPC476265
0.7927	Intermediate Similarity	NPC274522
0.7927	Intermediate Similarity	NPC206735
0.7927	Intermediate Similarity	NPC304194
0.7927	Intermediate Similarity	NPC472478
0.7922	Intermediate Similarity	NPC91369
0.7912	Intermediate Similarity	NPC10864
0.7907	Intermediate Similarity	NPC96496
0.7907	Intermediate Similarity	NPC264005
0.7907	Intermediate Similarity	NPC93778
0.7907	Intermediate Similarity	NPC269360
0.7901	Intermediate Similarity	NPC4827
0.7901	Intermediate Similarity	NPC321690
0.7901	Intermediate Similarity	NPC469996
0.7889	Intermediate Similarity	NPC33473
0.7889	Intermediate Similarity	NPC476174
0.7882	Intermediate Similarity	NPC190704
0.7882	Intermediate Similarity	NPC189311
0.7882	Intermediate Similarity	NPC471034
0.7882	Intermediate Similarity	NPC102292
0.7882	Intermediate Similarity	NPC2709
0.7875	Intermediate Similarity	NPC471046
0.7865	Intermediate Similarity	NPC287118
0.7865	Intermediate Similarity	NPC471902
0.7865	Intermediate Similarity	NPC473690
0.7865	Intermediate Similarity	NPC474185
0.7865	Intermediate Similarity	NPC475061
0.7857	Intermediate Similarity	NPC470047
0.7857	Intermediate Similarity	NPC475726
0.7857	Intermediate Similarity	NPC271784
0.7857	Intermediate Similarity	NPC472743
0.7857	Intermediate Similarity	NPC470046
0.7849	Intermediate Similarity	NPC46848
0.7849	Intermediate Similarity	NPC252614
0.7849	Intermediate Similarity	NPC52899
0.7849	Intermediate Similarity	NPC163963
0.7849	Intermediate Similarity	NPC289148
0.7848	Intermediate Similarity	NPC166797
0.7841	Intermediate Similarity	NPC8062
0.7841	Intermediate Similarity	NPC471896
0.7841	Intermediate Similarity	NPC328141
0.7831	Intermediate Similarity	NPC201912
0.7831	Intermediate Similarity	NPC278459
0.7831	Intermediate Similarity	NPC475951
0.7831	Intermediate Similarity	NPC471898
0.7831	Intermediate Similarity	NPC477372
0.7831	Intermediate Similarity	NPC38350
0.7826	Intermediate Similarity	NPC89099
0.7826	Intermediate Similarity	NPC474793
0.7821	Intermediate Similarity	NPC197701
0.7821	Intermediate Similarity	NPC469940
0.7821	Intermediate Similarity	NPC72343
0.7816	Intermediate Similarity	NPC183374
0.7816	Intermediate Similarity	NPC471900
0.7816	Intermediate Similarity	NPC472739
0.7816	Intermediate Similarity	NPC16377
0.7816	Intermediate Similarity	NPC211162
0.7816	Intermediate Similarity	NPC250687
0.7816	Intermediate Similarity	NPC254572
0.7816	Intermediate Similarity	NPC48824
0.7816	Intermediate Similarity	NPC146937
0.7816	Intermediate Similarity	NPC229407
0.7805	Intermediate Similarity	NPC44083
0.7805	Intermediate Similarity	NPC472490

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 NPC471475 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2030
0.2-0.3	4261
0.3-0.4	1804
0.4-0.5	458
0.5-0.6	186
0.6-0.7	145
0.7-0.8	84
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD6672	Approved
0.8452	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5737	Approved
0.8434	Intermediate Similarity	NPD6684	Approved
0.8434	Intermediate Similarity	NPD7521	Approved
0.8434	Intermediate Similarity	NPD7334	Approved
0.8434	Intermediate Similarity	NPD5330	Approved
0.8434	Intermediate Similarity	NPD6409	Approved
0.8434	Intermediate Similarity	NPD7146	Approved
0.8293	Intermediate Similarity	NPD4788	Approved
0.8235	Intermediate Similarity	NPD6903	Approved
0.8095	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD5777	Approved
0.8	Intermediate Similarity	NPD6098	Approved
0.7955	Intermediate Similarity	NPD8034	Phase 2
0.7955	Intermediate Similarity	NPD8035	Phase 2
0.7931	Intermediate Similarity	NPD6080	Approved
0.7931	Intermediate Similarity	NPD6673	Approved
0.7931	Intermediate Similarity	NPD6904	Approved
0.7865	Intermediate Similarity	NPD6399	Phase 3
0.7816	Intermediate Similarity	NPD5208	Approved
0.7738	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6083	Phase 2
0.7717	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4224	Phase 2
0.7582	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7900	Approved
0.7582	Intermediate Similarity	NPD7748	Approved
0.7558	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD5693	Phase 1
0.7556	Intermediate Similarity	NPD6050	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5695	Phase 3
0.7447	Intermediate Similarity	NPD5696	Approved
0.7444	Intermediate Similarity	NPD5207	Approved
0.7444	Intermediate Similarity	NPD5692	Phase 3
0.7407	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6001	Approved
0.7375	Intermediate Similarity	NPD6081	Approved
0.7363	Intermediate Similarity	NPD5694	Approved
0.7363	Intermediate Similarity	NPD6079	Approved
0.7363	Intermediate Similarity	NPD7515	Phase 2
0.7356	Intermediate Similarity	NPD3133	Approved
0.7356	Intermediate Similarity	NPD3665	Phase 1
0.7356	Intermediate Similarity	NPD3666	Approved
0.734	Intermediate Similarity	NPD7902	Approved
0.7333	Intermediate Similarity	NPD5328	Approved
0.7326	Intermediate Similarity	NPD3667	Approved
0.7326	Intermediate Similarity	NPD4221	Approved
0.7326	Intermediate Similarity	NPD4223	Phase 3
0.7317	Intermediate Similarity	NPD3702	Approved
0.7273	Intermediate Similarity	NPD5329	Approved
0.725	Intermediate Similarity	NPD4691	Approved
0.725	Intermediate Similarity	NPD4789	Approved
0.725	Intermediate Similarity	NPD4747	Approved
0.7229	Intermediate Similarity	NPD6117	Approved
0.72	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD6881	Approved
0.7191	Intermediate Similarity	NPD3618	Phase 1
0.7172	Intermediate Similarity	NPD7128	Approved
0.7172	Intermediate Similarity	NPD6675	Approved
0.7172	Intermediate Similarity	NPD5739	Approved
0.7172	Intermediate Similarity	NPD6402	Approved
0.716	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3668	Phase 3
0.7159	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7125	Intermediate Similarity	NPD4137	Phase 3
0.71	Intermediate Similarity	NPD5697	Approved
0.7083	Intermediate Similarity	NPD7638	Approved
0.7079	Intermediate Similarity	NPD1694	Approved
0.7059	Intermediate Similarity	NPD7290	Approved
0.7059	Intermediate Similarity	NPD6697	Approved
0.7059	Intermediate Similarity	NPD6114	Approved
0.7059	Intermediate Similarity	NPD6883	Approved
0.7059	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD7102	Approved
0.7059	Intermediate Similarity	NPD6118	Approved
0.7059	Intermediate Similarity	NPD3617	Approved
0.7053	Intermediate Similarity	NPD7732	Phase 3
0.7051	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4244	Approved
0.7037	Intermediate Similarity	NPD4245	Approved
0.703	Intermediate Similarity	NPD6011	Approved
0.703	Intermediate Similarity	NPD7320	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD5279	Phase 3
0.7	Intermediate Similarity	NPD6008	Approved
0.7	Intermediate Similarity	NPD4689	Approved
0.7	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD5205	Approved
0.7	Intermediate Similarity	NPD5360	Phase 3
0.7	Intermediate Similarity	NPD4693	Phase 3
0.7	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4690	Approved
0.699	Remote Similarity	NPD6617	Approved
0.699	Remote Similarity	NPD6847	Approved
0.699	Remote Similarity	NPD8130	Phase 1
0.699	Remote Similarity	NPD6649	Approved
0.699	Remote Similarity	NPD6869	Approved
0.699	Remote Similarity	NPD6650	Approved
0.6989	Remote Similarity	NPD5284	Approved
0.6989	Remote Similarity	NPD5281	Approved
0.6988	Remote Similarity	NPD5733	Approved
0.6988	Remote Similarity	NPD4058	Approved
0.697	Remote Similarity	NPD6052	Approved
0.6961	Remote Similarity	NPD6373	Approved
0.6961	Remote Similarity	NPD6014	Approved
0.6961	Remote Similarity	NPD6012	Approved
0.6961	Remote Similarity	NPD6013	Approved
0.6961	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6051	Approved
0.6957	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4629	Approved
0.6947	Remote Similarity	NPD5654	Approved
0.6947	Remote Similarity	NPD5210	Approved
0.6931	Remote Similarity	NPD5701	Approved
0.6931	Remote Similarity	NPD6614	Approved
0.6923	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD8297	Approved
0.6915	Remote Similarity	NPD4202	Approved
0.6914	Remote Similarity	NPD3698	Phase 2
0.6914	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4695	Discontinued
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5221	Approved
0.6827	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4694	Approved
0.6813	Remote Similarity	NPD5280	Approved
0.6804	Remote Similarity	NPD5959	Approved
0.6804	Remote Similarity	NPD5173	Approved
0.679	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4687	Approved
0.6782	Remote Similarity	NPD4195	Approved
0.6747	Remote Similarity	NPD5276	Approved
0.6729	Remote Similarity	NPD6868	Approved
0.6701	Remote Similarity	NPD4697	Phase 3
0.6701	Remote Similarity	NPD7614	Phase 1
0.6698	Remote Similarity	NPD6858	Approved
0.6698	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD4755	Approved
0.663	Remote Similarity	NPD4519	Discontinued
0.663	Remote Similarity	NPD4623	Approved
0.6629	Remote Similarity	NPD4139	Approved
0.6629	Remote Similarity	NPD4692	Approved
0.6606	Remote Similarity	NPD6335	Approved
0.6602	Remote Similarity	NPD6412	Phase 2
0.66	Remote Similarity	NPD5223	Approved
0.6574	Remote Similarity	NPD6274	Approved
0.6548	Remote Similarity	NPD4758	Discontinued
0.6545	Remote Similarity	NPD7100	Approved
0.6545	Remote Similarity	NPD7101	Approved
0.6542	Remote Similarity	NPD8133	Approved
0.6542	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD5224	Approved
0.6535	Remote Similarity	NPD5226	Approved
0.6535	Remote Similarity	NPD5225	Approved
0.6535	Remote Similarity	NPD4633	Approved
0.6535	Remote Similarity	NPD5211	Phase 2
0.6531	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7525	Registered
0.6514	Remote Similarity	NPD6317	Approved
0.6512	Remote Similarity	NPD7339	Approved
0.6512	Remote Similarity	NPD8039	Approved
0.6512	Remote Similarity	NPD6942	Approved
0.6512	Remote Similarity	NPD3703	Phase 2
0.65	Remote Similarity	NPD4700	Approved
0.65	Remote Similarity	NPD6404	Discontinued
0.6477	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5175	Approved
0.6471	Remote Similarity	NPD5174	Approved
0.6458	Remote Similarity	NPD6411	Approved
0.6455	Remote Similarity	NPD6314	Approved
0.6455	Remote Similarity	NPD6313	Approved
0.6408	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD6009	Approved
0.6354	Remote Similarity	NPD4096	Approved
0.6353	Remote Similarity	NPD4243	Approved
0.6339	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD7604	Phase 2
0.6311	Remote Similarity	NPD4754	Approved
0.6292	Remote Similarity	NPD5364	Discontinued
0.6292	Remote Similarity	NPD3671	Phase 1
0.6289	Remote Similarity	NPD7637	Suspended
0.6283	Remote Similarity	NPD6908	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