NPASS Compound

Structure

CID274996 OpenBabel06191716082D 35 37 0 0 1 0 0 0 0 0999 V2000 -4.8126 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 -3.8344 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 4 20 1 0 0 0 0 5 21 2 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 26 2 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 25 2 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 22 10 1 6 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 1 0 0 0 24 30 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	140.16
Volume:	172.96
LogP:	5.212
LogD:	4.299
LogS:	-5.341
# Rotatable Bonds:	3
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	1.657
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.415
MDCK Permeability:	1.5094234186108224e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.422
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734
Plasma Protein Binding (PPB):	96.897216796875%
Volume Distribution (VD):	2.732
Pgp-substrate:	1.9583040475845337%

ADMET: Metabolism

CYP1A2-inhibitor:	0.886
CYP1A2-substrate:	0.494
CYP2C19-inhibitor:	0.588
CYP2C19-substrate:	0.334
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.266
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.268
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	6.222
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.194
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.89
Carcinogencity:	0.068
Eye Corrosion:	0.99
Eye Irritation:	0.987
Respiratory Toxicity:	0.394

Download Data

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

Natural Product: NPC274996

Natural Product ID:	NPC274996
*Common Name:**	Poricoic Acid C
IUPAC Name:	(2R)-2-[(3R,3aR,6S,7S,9bR)-6-(2-carboxyethyl)-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,7,8-hexahydrocyclopenta[a]naphthalen-3-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	Poricoic Acid C
Standard InCHIKey:	QFVFCBZDUKVXLR-PKSIZLAPSA-N
Standard InCHI:	InChI=1S/C31H46O4/c1-19(2)21(5)9-10-22(28(34)35)24-13-17-31(8)26-12-11-23(20(3)4)29(6,16-15-27(32)33)25(26)14-18-30(24,31)7/h12,14,19,22-24H,3,5,9-11,13,15-18H2,1-2,4,6-8H3,(H,32,33)(H,34,35)/p-2/t22-,23+,24-,29+,30-,31+/m1/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1CC[C@@]2(C)C3=CC[C@@H](C(=C)C)[C@](C)(CCC(=O)[O-])C3=CC[C@]12C)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1793863
PubChem CID:	56668247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33546	Poria coco	Species		Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8
Others	5

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[548979]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	14500.0	nM	PMID[548980]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	23900.0	nM	PMID[548980]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	25900.0	nM	PMID[548980]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	27000.0	nM	PMID[548980]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	53100.0	nM	PMID[548980]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	68900.0	nM	PMID[548980]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[548979]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	21.1	%	PMID[548979]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	67.2	%	PMID[548979]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	91.7	%	PMID[548979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45900.0	nM	PMID[548980]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[548980]

☑ 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 NPC274996 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	151
0.1-0.2	986
0.2-0.3	6378
0.3-0.4	16421
0.4-0.5	8172
0.5-0.6	6973
0.6-0.7	3049
0.7-0.8	499
0.8-0.85	43
0.85-0.9	20
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196827
0.9605	High Similarity	NPC296367
0.9481	High Similarity	NPC310470
0.9231	High Similarity	NPC83569
0.9231	High Similarity	NPC69279
0.9054	High Similarity	NPC301065
0.8974	High Similarity	NPC201912
0.8974	High Similarity	NPC38350
0.8961	High Similarity	NPC477371
0.8902	High Similarity	NPC247406
0.8902	High Similarity	NPC48866
0.8861	High Similarity	NPC260956
0.8861	High Similarity	NPC133391
0.8816	High Similarity	NPC309399
0.875	High Similarity	NPC477373
0.8734	High Similarity	NPC147066
0.8734	High Similarity	NPC477372
0.8718	High Similarity	NPC158846
0.869	High Similarity	NPC46281
0.869	High Similarity	NPC123854
0.8642	High Similarity	NPC164577
0.8588	High Similarity	NPC204341
0.8588	High Similarity	NPC45269
0.8571	High Similarity	NPC84271
0.8571	High Similarity	NPC77168
0.8571	High Similarity	NPC102414
0.8554	High Similarity	NPC312215
0.8553	High Similarity	NPC306928
0.8533	High Similarity	NPC160817
0.8519	High Similarity	NPC470015
0.8519	High Similarity	NPC167103
0.8519	High Similarity	NPC97913
0.8519	High Similarity	NPC168188
0.8488	Intermediate Similarity	NPC152897
0.8488	Intermediate Similarity	NPC66429
0.8452	Intermediate Similarity	NPC294480
0.8442	Intermediate Similarity	NPC476844
0.8434	Intermediate Similarity	NPC212843
0.8415	Intermediate Similarity	NPC472865
0.8415	Intermediate Similarity	NPC165064
0.8395	Intermediate Similarity	NPC320514
0.8391	Intermediate Similarity	NPC469406
0.8391	Intermediate Similarity	NPC7165
0.8354	Intermediate Similarity	NPC260385
0.8354	Intermediate Similarity	NPC280654
0.8354	Intermediate Similarity	NPC110094
0.8354	Intermediate Similarity	NPC321514
0.8354	Intermediate Similarity	NPC74410
0.8333	Intermediate Similarity	NPC187376
0.8333	Intermediate Similarity	NPC159046
0.8333	Intermediate Similarity	NPC233836
0.8333	Intermediate Similarity	NPC899
0.8333	Intermediate Similarity	NPC246445
0.8333	Intermediate Similarity	NPC167877
0.8333	Intermediate Similarity	NPC96496
0.8333	Intermediate Similarity	NPC136948
0.8313	Intermediate Similarity	NPC94531
0.8313	Intermediate Similarity	NPC269638
0.8313	Intermediate Similarity	NPC123319
0.8313	Intermediate Similarity	NPC311702
0.8313	Intermediate Similarity	NPC29447
0.8312	Intermediate Similarity	NPC237591
0.8312	Intermediate Similarity	NPC3753
0.8312	Intermediate Similarity	NPC55527
0.8295	Intermediate Similarity	NPC162001
0.8295	Intermediate Similarity	NPC45324
0.8295	Intermediate Similarity	NPC263347
0.8295	Intermediate Similarity	NPC171395
0.8295	Intermediate Similarity	NPC222845
0.8295	Intermediate Similarity	NPC20546
0.8272	Intermediate Similarity	NPC142244
0.8256	Intermediate Similarity	NPC111585
0.8256	Intermediate Similarity	NPC175628
0.8256	Intermediate Similarity	NPC148414
0.825	Intermediate Similarity	NPC199595
0.825	Intermediate Similarity	NPC327674
0.8235	Intermediate Similarity	NPC183546
0.8235	Intermediate Similarity	NPC242864
0.8228	Intermediate Similarity	NPC471899
0.8228	Intermediate Similarity	NPC471897
0.8228	Intermediate Similarity	NPC107039
0.8214	Intermediate Similarity	NPC55309
0.8214	Intermediate Similarity	NPC186975
0.8214	Intermediate Similarity	NPC155011
0.8214	Intermediate Similarity	NPC28252
0.8205	Intermediate Similarity	NPC192540
0.8205	Intermediate Similarity	NPC279666
0.8202	Intermediate Similarity	NPC155676
0.8193	Intermediate Similarity	NPC476038
0.8193	Intermediate Similarity	NPC19849
0.8193	Intermediate Similarity	NPC472864
0.8193	Intermediate Similarity	NPC194937
0.8171	Intermediate Similarity	NPC240302
0.8161	Intermediate Similarity	NPC26888
0.8148	Intermediate Similarity	NPC104545
0.8148	Intermediate Similarity	NPC37038
0.814	Intermediate Similarity	NPC474704
0.814	Intermediate Similarity	NPC262043
0.814	Intermediate Similarity	NPC474570
0.814	Intermediate Similarity	NPC214387
0.814	Intermediate Similarity	NPC474889
0.814	Intermediate Similarity	NPC475921
0.814	Intermediate Similarity	NPC155479
0.814	Intermediate Similarity	NPC54689
0.8125	Intermediate Similarity	NPC4827
0.8125	Intermediate Similarity	NPC179028
0.8118	Intermediate Similarity	NPC474684
0.8118	Intermediate Similarity	NPC236618
0.8118	Intermediate Similarity	NPC142361
0.8118	Intermediate Similarity	NPC128644
0.8111	Intermediate Similarity	NPC469432
0.8101	Intermediate Similarity	NPC180886
0.8101	Intermediate Similarity	NPC89294
0.8101	Intermediate Similarity	NPC69143
0.8095	Intermediate Similarity	NPC473038
0.8095	Intermediate Similarity	NPC11711
0.8095	Intermediate Similarity	NPC283733
0.8077	Intermediate Similarity	NPC476046
0.8077	Intermediate Similarity	NPC103958
0.8077	Intermediate Similarity	NPC251970
0.8077	Intermediate Similarity	NPC161923
0.8077	Intermediate Similarity	NPC213223
0.8077	Intermediate Similarity	NPC183503
0.8077	Intermediate Similarity	NPC283908
0.8077	Intermediate Similarity	NPC241854
0.8072	Intermediate Similarity	NPC70834
0.8072	Intermediate Similarity	NPC477852
0.8049	Intermediate Similarity	NPC278459
0.8049	Intermediate Similarity	NPC327002
0.8049	Intermediate Similarity	NPC221647
0.8046	Intermediate Similarity	NPC469400
0.8046	Intermediate Similarity	NPC477149
0.8046	Intermediate Similarity	NPC477147
0.8046	Intermediate Similarity	NPC471896
0.8025	Intermediate Similarity	NPC231431
0.8025	Intermediate Similarity	NPC16394
0.8025	Intermediate Similarity	NPC215843
0.8023	Intermediate Similarity	NPC44181
0.8023	Intermediate Similarity	NPC117122
0.8022	Intermediate Similarity	NPC186810
0.8022	Intermediate Similarity	NPC477813
0.8022	Intermediate Similarity	NPC235464
0.8022	Intermediate Similarity	NPC166745
0.8022	Intermediate Similarity	NPC48647
0.8	Intermediate Similarity	NPC66105
0.8	Intermediate Similarity	NPC68828
0.8	Intermediate Similarity	NPC89077
0.8	Intermediate Similarity	NPC6247
0.8	Intermediate Similarity	NPC472869
0.7978	Intermediate Similarity	NPC49670
0.7976	Intermediate Similarity	NPC100391
0.7976	Intermediate Similarity	NPC473246
0.7976	Intermediate Similarity	NPC87552
0.7976	Intermediate Similarity	NPC209882
0.7975	Intermediate Similarity	NPC476795
0.7955	Intermediate Similarity	NPC297265
0.7955	Intermediate Similarity	NPC154101
0.7955	Intermediate Similarity	NPC474018
0.7955	Intermediate Similarity	NPC189520
0.7955	Intermediate Similarity	NPC23434
0.7955	Intermediate Similarity	NPC473986
0.7952	Intermediate Similarity	NPC321289
0.7952	Intermediate Similarity	NPC327969
0.7952	Intermediate Similarity	NPC15910
0.7949	Intermediate Similarity	NPC330659
0.7949	Intermediate Similarity	NPC244708
0.7949	Intermediate Similarity	NPC161187
0.7931	Intermediate Similarity	NPC476733
0.7931	Intermediate Similarity	NPC66344
0.7931	Intermediate Similarity	NPC215029
0.7927	Intermediate Similarity	NPC477057
0.7907	Intermediate Similarity	NPC136548
0.7901	Intermediate Similarity	NPC169095
0.7901	Intermediate Similarity	NPC321690
0.7895	Intermediate Similarity	NPC290445
0.7895	Intermediate Similarity	NPC36616
0.7882	Intermediate Similarity	NPC76333
0.7882	Intermediate Similarity	NPC474083
0.7882	Intermediate Similarity	NPC142649
0.7875	Intermediate Similarity	NPC20466
0.7865	Intermediate Similarity	NPC470375
0.7865	Intermediate Similarity	NPC472942
0.7865	Intermediate Similarity	NPC243866
0.7865	Intermediate Similarity	NPC470376
0.7865	Intermediate Similarity	NPC206810
0.7857	Intermediate Similarity	NPC49019
0.7857	Intermediate Similarity	NPC200752
0.7849	Intermediate Similarity	NPC146822
0.7849	Intermediate Similarity	NPC99411
0.7841	Intermediate Similarity	NPC69622
0.7841	Intermediate Similarity	NPC129913
0.7838	Intermediate Similarity	NPC234767
0.7831	Intermediate Similarity	NPC162632
0.7831	Intermediate Similarity	NPC263272
0.7831	Intermediate Similarity	NPC232625
0.7831	Intermediate Similarity	NPC471898
0.7831	Intermediate Similarity	NPC274050
0.7831	Intermediate Similarity	NPC267691
0.7826	Intermediate Similarity	NPC471717
0.7816	Intermediate Similarity	NPC24816

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 NPC274996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	1520
0.2-0.3	4157
0.3-0.4	2244
0.4-0.5	619
0.5-0.6	256
0.6-0.7	190
0.7-0.8	32
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD5284	Approved
0.8372	Intermediate Similarity	NPD5281	Approved
0.8	Intermediate Similarity	NPD5280	Approved
0.8	Intermediate Similarity	NPD4694	Approved
0.7955	Intermediate Similarity	NPD6050	Approved
0.7865	Intermediate Similarity	NPD6399	Phase 3
0.7841	Intermediate Similarity	NPD5692	Phase 3
0.7791	Intermediate Similarity	NPD5279	Phase 3
0.7765	Intermediate Similarity	NPD4786	Approved
0.7753	Intermediate Similarity	NPD5694	Approved
0.7742	Intermediate Similarity	NPD6404	Discontinued
0.7738	Intermediate Similarity	NPD4223	Phase 3
0.7738	Intermediate Similarity	NPD4221	Approved
0.7727	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5695	Phase 3
0.7674	Intermediate Similarity	NPD5329	Approved
0.764	Intermediate Similarity	NPD5207	Approved
0.7625	Intermediate Similarity	NPD5733	Approved
0.7614	Intermediate Similarity	NPD5737	Approved
0.7614	Intermediate Similarity	NPD6672	Approved
0.7586	Intermediate Similarity	NPD6098	Approved
0.7586	Intermediate Similarity	NPD5690	Phase 2
0.7558	Intermediate Similarity	NPD4197	Approved
0.7529	Intermediate Similarity	NPD3667	Approved
0.7528	Intermediate Similarity	NPD6673	Approved
0.7528	Intermediate Similarity	NPD6080	Approved
0.7528	Intermediate Similarity	NPD6904	Approved
0.7527	Intermediate Similarity	NPD6084	Phase 2
0.7527	Intermediate Similarity	NPD6083	Phase 2
0.747	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4096	Approved
0.7416	Intermediate Similarity	NPD4518	Approved
0.7412	Intermediate Similarity	NPD4692	Approved
0.7412	Intermediate Similarity	NPD4139	Approved
0.7407	Intermediate Similarity	NPD4687	Approved
0.7386	Intermediate Similarity	NPD4138	Approved
0.7386	Intermediate Similarity	NPD4689	Approved
0.7386	Intermediate Similarity	NPD4693	Phase 3
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD4688	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7386	Intermediate Similarity	NPD5205	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD4690	Approved
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7375	Intermediate Similarity	NPD5276	Approved
0.7363	Intermediate Similarity	NPD6411	Approved
0.7356	Intermediate Similarity	NPD3666	Approved
0.7356	Intermediate Similarity	NPD3665	Phase 1
0.7356	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD5328	Approved
0.7312	Intermediate Similarity	NPD5654	Approved
0.7283	Intermediate Similarity	NPD5133	Approved
0.7273	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5696	Approved
0.7262	Intermediate Similarity	NPD3617	Approved
0.7222	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5208	Approved
0.7222	Intermediate Similarity	NPD6903	Approved
0.7191	Intermediate Similarity	NPD3618	Phase 1
0.7191	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7515	Phase 2
0.7174	Intermediate Similarity	NPD6079	Approved
0.7174	Intermediate Similarity	NPD5693	Phase 1
0.716	Intermediate Similarity	NPD4243	Approved
0.7159	Intermediate Similarity	NPD3668	Phase 3
0.7158	Intermediate Similarity	NPD5959	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4695	Discontinued
0.7045	Intermediate Similarity	NPD5362	Discontinued
0.7037	Intermediate Similarity	NPD4747	Approved
0.7021	Intermediate Similarity	NPD7748	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.6989	Remote Similarity	NPD8035	Phase 2
0.6989	Remote Similarity	NPD8034	Phase 2
0.6988	Remote Similarity	NPD6924	Approved
0.6988	Remote Similarity	NPD4785	Approved
0.6988	Remote Similarity	NPD4784	Approved
0.6988	Remote Similarity	NPD4058	Approved
0.6988	Remote Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD4195	Approved
0.6951	Remote Similarity	NPD6081	Approved
0.6947	Remote Similarity	NPD5210	Approved
0.6947	Remote Similarity	NPD4629	Approved
0.6932	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5778	Approved
0.6915	Remote Similarity	NPD4202	Approved
0.6915	Remote Similarity	NPD5779	Approved
0.6914	Remote Similarity	NPD4137	Phase 3
0.6905	Remote Similarity	NPD7339	Approved
0.6905	Remote Similarity	NPD6942	Approved
0.6905	Remote Similarity	NPD8039	Approved
0.6897	Remote Similarity	NPD5368	Approved
0.6875	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD7614	Phase 1
0.6875	Remote Similarity	NPD5221	Approved
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7320	Approved
0.6863	Remote Similarity	NPD6899	Approved
0.6863	Remote Similarity	NPD6881	Approved
0.6854	Remote Similarity	NPD4788	Approved
0.6842	Remote Similarity	NPD6001	Approved
0.6829	Remote Similarity	NPD4691	Approved
0.6824	Remote Similarity	NPD6933	Approved
0.6818	Remote Similarity	NPD857	Phase 3
0.6818	Remote Similarity	NPD5369	Approved
0.6813	Remote Similarity	NPD4623	Approved
0.6813	Remote Similarity	NPD4519	Discontinued
0.6809	Remote Similarity	NPD7637	Suspended
0.6804	Remote Similarity	NPD5173	Approved
0.6804	Remote Similarity	NPD4755	Approved
0.6804	Remote Similarity	NPD7902	Approved
0.6796	Remote Similarity	NPD6373	Approved
0.6796	Remote Similarity	NPD6372	Approved
0.679	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5701	Approved
0.6765	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD4224	Phase 2
0.675	Remote Similarity	NPD7331	Phase 2
0.6742	Remote Similarity	NPD4270	Approved
0.6742	Remote Similarity	NPD6435	Approved
0.6742	Remote Similarity	NPD4269	Approved
0.6735	Remote Similarity	NPD7638	Approved
0.6731	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD7102	Approved
0.6731	Remote Similarity	NPD7290	Approved
0.6707	Remote Similarity	NPD6923	Approved
0.6707	Remote Similarity	NPD6922	Approved
0.6706	Remote Similarity	NPD5275	Approved
0.6706	Remote Similarity	NPD4190	Phase 3
0.6705	Remote Similarity	NPD7525	Registered
0.6699	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6635	Remote Similarity	NPD6013	Approved
0.6635	Remote Similarity	NPD6012	Approved
0.6635	Remote Similarity	NPD6014	Approved
0.6634	Remote Similarity	NPD6052	Approved
0.6629	Remote Similarity	NPD4790	Discontinued
0.6628	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6117	Approved
0.6627	Remote Similarity	NPD7144	Approved
0.6627	Remote Similarity	NPD7143	Approved
0.6625	Remote Similarity	NPD7341	Phase 2
0.6622	Remote Similarity	NPD4266	Approved
0.6622	Remote Similarity	NPD3194	Approved
0.6622	Remote Similarity	NPD3196	Approved
0.6622	Remote Similarity	NPD3195	Phase 2
0.6604	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.66	Remote Similarity	NPD5223	Approved
0.6596	Remote Similarity	NPD6051	Approved
0.6591	Remote Similarity	NPD6929	Approved
0.6588	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3573	Approved
0.6552	Remote Similarity	NPD6116	Phase 1
0.6548	Remote Similarity	NPD7151	Approved
0.6548	Remote Similarity	NPD7150	Approved
0.6548	Remote Similarity	NPD7152	Approved
0.6535	Remote Similarity	NPD5091	Approved
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
0.6526	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD5363	Approved
0.6517	Remote Similarity	NPD6931	Approved
0.6517	Remote Similarity	NPD4819	Approved
0.6517	Remote Similarity	NPD4821	Approved
0.6517	Remote Similarity	NPD4252	Approved
0.6517	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6930	Phase 2
0.6517	Remote Similarity	NPD4822	Approved
0.6517	Remote Similarity	NPD4820	Approved
0.6495	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7900	Approved
0.6486	Remote Similarity	NPD3172	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