NPASS Compound

Structure

CID19856 OpenBabel06191715342D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 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 1.5000 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 0.0000 -1.0000 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 -2.7321 -0.0000 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 2.5981 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 1 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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	3.708
LogD:	3.131
LogS:	-4.089
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.869
Synthetic Accessibility Score:	3.697
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.629
MDCK Permeability:	1.7473508705734275e-05
Pgp-inhibitor:	0.428
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.8
30% Bioavailability (F30%):	0.767

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	92.21373748779297%
Volume Distribution (VD):	1.492
Pgp-substrate:	5.364383697509766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.398
CYP2D6-inhibitor:	0.138
CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.593
CYP3A4-substrate:	0.563

ADMET: Excretion

Clearance (CL):	7.357
Half-life (T1/2):	0.175

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.436
Skin Sensitization:	0.669
Carcinogencity:	0.037
Eye Corrosion:	0.006
Eye Irritation:	0.252
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC19856

Natural Product ID:	NPC19856
*Common Name:**	8,11,13-Abietatriene-15,18-Diol
IUPAC Name:	2-[(4bS,8R,8aR)-8-(hydroxymethyl)-4b,8-dimethyl-5,6,7,8a,9,10-hexahydrophenanthren-2-yl]propan-2-ol
Synonyms:
Standard InCHIKey:	FKCPLBHSZGVMNG-YSIASYRMSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-18(2,22)15-7-8-16-14(12-15)6-9-17-19(3,13-21)10-5-11-20(16,17)4/h7-8,12,17,21-22H,5-6,9-11,13H2,1-4H3/t17-,19-,20+/m0/s1
SMILES:	CC(C)(c1ccc2c(CC[C@H]3[C@@](C)(CCC[C@]23C)CO)c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL601734
PubChem CID:	11392488
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2089121]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379416]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3443857]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3760882]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3841557]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288443]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8133299]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[8133299]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691212]
NPO22470	Corynebacterium glutamicum	Species	Corynebacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[Article]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21165	Phagnalon atlanticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17292	Asparagus racemosus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20619	Ougeinia dalbergioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19502	Squamopappus skutchii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22470	Corynebacterium glutamicum	Species	Corynebacteriaceae	Bacteria	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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[534191]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[534191]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[534191]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[534191]

☑ 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 NPC19856 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	205
0.1-0.2	1210
0.2-0.3	2338
0.3-0.4	8632
0.4-0.5	14752
0.5-0.6	12110
0.6-0.7	2920
0.7-0.8	437
0.8-0.85	62
0.85-0.9	20
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9596	High Similarity	NPC472979
0.9596	High Similarity	NPC27252
0.94	High Similarity	NPC472980
0.9394	High Similarity	NPC243601
0.9307	High Similarity	NPC472982
0.9307	High Similarity	NPC149455
0.9307	High Similarity	NPC64642
0.9038	High Similarity	NPC471188
0.8947	High Similarity	NPC220596
0.8796	High Similarity	NPC212891
0.8762	High Similarity	NPC95126
0.8762	High Similarity	NPC475002
0.8737	High Similarity	NPC1793
0.8687	High Similarity	NPC324602
0.866	High Similarity	NPC128645
0.8641	High Similarity	NPC471133
0.8641	High Similarity	NPC471186
0.8624	High Similarity	NPC469663
0.8624	High Similarity	NPC242764
0.8624	High Similarity	NPC105141
0.8624	High Similarity	NPC92
0.8624	High Similarity	NPC472862
0.8614	High Similarity	NPC289117
0.8585	High Similarity	NPC133308
0.8544	High Similarity	NPC56168
0.8544	High Similarity	NPC315794
0.8532	High Similarity	NPC192948
0.8532	High Similarity	NPC35797
0.8455	Intermediate Similarity	NPC308311
0.8455	Intermediate Similarity	NPC477137
0.8455	Intermediate Similarity	NPC38893
0.8455	Intermediate Similarity	NPC219112
0.844	Intermediate Similarity	NPC221275
0.844	Intermediate Similarity	NPC268160
0.8431	Intermediate Similarity	NPC469481
0.8421	Intermediate Similarity	NPC474211
0.8421	Intermediate Similarity	NPC93843
0.8381	Intermediate Similarity	NPC142326
0.8381	Intermediate Similarity	NPC94751
0.8378	Intermediate Similarity	NPC304510
0.8378	Intermediate Similarity	NPC172219
0.8378	Intermediate Similarity	NPC477136
0.8378	Intermediate Similarity	NPC45794
0.8367	Intermediate Similarity	NPC79917
0.8364	Intermediate Similarity	NPC147179
0.8364	Intermediate Similarity	NPC469719
0.8351	Intermediate Similarity	NPC199567
0.8333	Intermediate Similarity	NPC369
0.8333	Intermediate Similarity	NPC111108
0.8333	Intermediate Similarity	NPC293831
0.8319	Intermediate Similarity	NPC133389
0.8319	Intermediate Similarity	NPC183339
0.8319	Intermediate Similarity	NPC234337
0.8316	Intermediate Similarity	NPC474354
0.8304	Intermediate Similarity	NPC254233
0.8304	Intermediate Similarity	NPC471671
0.8288	Intermediate Similarity	NPC308828
0.8283	Intermediate Similarity	NPC314690
0.8241	Intermediate Similarity	NPC132720
0.823	Intermediate Similarity	NPC469644
0.8211	Intermediate Similarity	NPC168855
0.819	Intermediate Similarity	NPC77691
0.819	Intermediate Similarity	NPC472222
0.819	Intermediate Similarity	NPC472221
0.8165	Intermediate Similarity	NPC260323
0.8165	Intermediate Similarity	NPC176279
0.8165	Intermediate Similarity	NPC471189
0.8142	Intermediate Similarity	NPC48342
0.8142	Intermediate Similarity	NPC164649
0.8142	Intermediate Similarity	NPC469609
0.8125	Intermediate Similarity	NPC471668
0.8108	Intermediate Similarity	NPC195922
0.8105	Intermediate Similarity	NPC172984
0.8103	Intermediate Similarity	NPC182333
0.8103	Intermediate Similarity	NPC273336
0.8091	Intermediate Similarity	NPC228425
0.8091	Intermediate Similarity	NPC250323
0.8087	Intermediate Similarity	NPC472981
0.8073	Intermediate Similarity	NPC141782
0.8056	Intermediate Similarity	NPC11554
0.8021	Intermediate Similarity	NPC304538
0.8	Intermediate Similarity	NPC77772
0.8	Intermediate Similarity	NPC322753
0.7983	Intermediate Similarity	NPC5486
0.7983	Intermediate Similarity	NPC253681
0.7982	Intermediate Similarity	NPC154030
0.7946	Intermediate Similarity	NPC471534
0.7944	Intermediate Similarity	NPC117115
0.7931	Intermediate Similarity	NPC328504
0.7928	Intermediate Similarity	NPC46940
0.7913	Intermediate Similarity	NPC126002
0.7913	Intermediate Similarity	NPC93071
0.7913	Intermediate Similarity	NPC151197
0.7909	Intermediate Similarity	NPC265513
0.7909	Intermediate Similarity	NPC13482
0.7905	Intermediate Similarity	NPC225079
0.7905	Intermediate Similarity	NPC136810
0.7905	Intermediate Similarity	NPC133809
0.7905	Intermediate Similarity	NPC245927
0.7905	Intermediate Similarity	NPC128248
0.7895	Intermediate Similarity	NPC242628
0.7895	Intermediate Similarity	NPC133050
0.7881	Intermediate Similarity	NPC471187
0.7881	Intermediate Similarity	NPC85511
0.7863	Intermediate Similarity	NPC142198
0.7863	Intermediate Similarity	NPC269923
0.7863	Intermediate Similarity	NPC167323
0.7863	Intermediate Similarity	NPC77569
0.7857	Intermediate Similarity	NPC196673
0.7857	Intermediate Similarity	NPC169616
0.7857	Intermediate Similarity	NPC715
0.7845	Intermediate Similarity	NPC260832
0.7845	Intermediate Similarity	NPC135467
0.7838	Intermediate Similarity	NPC266937
0.7838	Intermediate Similarity	NPC95716
0.7838	Intermediate Similarity	NPC470770
0.7835	Intermediate Similarity	NPC95429
0.783	Intermediate Similarity	NPC51015
0.7815	Intermediate Similarity	NPC181334
0.7812	Intermediate Similarity	NPC103326
0.7812	Intermediate Similarity	NPC87299
0.7812	Intermediate Similarity	NPC99394
0.7812	Intermediate Similarity	NPC329319
0.7807	Intermediate Similarity	NPC137496
0.7807	Intermediate Similarity	NPC154511
0.7807	Intermediate Similarity	NPC247858
0.7807	Intermediate Similarity	NPC257540
0.7807	Intermediate Similarity	NPC141001
0.7807	Intermediate Similarity	NPC474358
0.7807	Intermediate Similarity	NPC474387
0.7798	Intermediate Similarity	NPC21929
0.7798	Intermediate Similarity	NPC151477
0.7797	Intermediate Similarity	NPC152946
0.7797	Intermediate Similarity	NPC471794
0.7797	Intermediate Similarity	NPC11250
0.7788	Intermediate Similarity	NPC93181
0.7769	Intermediate Similarity	NPC115797
0.7769	Intermediate Similarity	NPC51448
0.7768	Intermediate Similarity	NPC62867
0.7768	Intermediate Similarity	NPC302371
0.7768	Intermediate Similarity	NPC177962
0.7755	Intermediate Similarity	NPC99482
0.775	Intermediate Similarity	NPC4286
0.775	Intermediate Similarity	NPC76119
0.7748	Intermediate Similarity	NPC474057
0.7739	Intermediate Similarity	NPC16030
0.7731	Intermediate Similarity	NPC307139
0.7731	Intermediate Similarity	NPC198014
0.7727	Intermediate Similarity	NPC475006
0.7712	Intermediate Similarity	NPC253627
0.7708	Intermediate Similarity	NPC117180
0.7706	Intermediate Similarity	NPC271274
0.7692	Intermediate Similarity	NPC99734
0.7692	Intermediate Similarity	NPC21959
0.7686	Intermediate Similarity	NPC321822
0.7686	Intermediate Similarity	NPC325294
0.7685	Intermediate Similarity	NPC475225
0.7685	Intermediate Similarity	NPC238696
0.7685	Intermediate Similarity	NPC323810
0.7677	Intermediate Similarity	NPC243166
0.7672	Intermediate Similarity	NPC206
0.7658	Intermediate Similarity	NPC58865
0.7647	Intermediate Similarity	NPC478058
0.7647	Intermediate Similarity	NPC71094
0.7647	Intermediate Similarity	NPC321402
0.7642	Intermediate Similarity	NPC92730
0.7642	Intermediate Similarity	NPC221825
0.7636	Intermediate Similarity	NPC320439
0.7636	Intermediate Similarity	NPC66834
0.7632	Intermediate Similarity	NPC186933
0.7632	Intermediate Similarity	NPC215419
0.7629	Intermediate Similarity	NPC283012
0.7629	Intermediate Similarity	NPC475199
0.7627	Intermediate Similarity	NPC32322
0.7627	Intermediate Similarity	NPC259703
0.7623	Intermediate Similarity	NPC471077
0.7611	Intermediate Similarity	NPC470253
0.7607	Intermediate Similarity	NPC42657
0.7607	Intermediate Similarity	NPC323074
0.7607	Intermediate Similarity	NPC476645
0.7607	Intermediate Similarity	NPC238582
0.7604	Intermediate Similarity	NPC328178
0.7603	Intermediate Similarity	NPC87985
0.7603	Intermediate Similarity	NPC124030
0.7603	Intermediate Similarity	NPC137750
0.7596	Intermediate Similarity	NPC289769
0.7593	Intermediate Similarity	NPC471228
0.7593	Intermediate Similarity	NPC235762
0.7589	Intermediate Similarity	NPC296683
0.7579	Intermediate Similarity	NPC224544
0.757	Intermediate Similarity	NPC294741
0.757	Intermediate Similarity	NPC225506
0.757	Intermediate Similarity	NPC211885
0.757	Intermediate Similarity	NPC72729
0.7568	Intermediate Similarity	NPC262365
0.7565	Intermediate Similarity	NPC246760
0.7565	Intermediate Similarity	NPC84999
0.7563	Intermediate Similarity	NPC162935
0.7563	Intermediate Similarity	NPC249340
0.7563	Intermediate Similarity	NPC475166

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 NPC19856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	901
0.2-0.3	1116
0.3-0.4	2884
0.4-0.5	2369
0.5-0.6	1262
0.6-0.7	357
0.7-0.8	56
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8812	High Similarity	NPD5700	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.8142	Intermediate Similarity	NPD7741	Discontinued
0.8142	Intermediate Similarity	NPD3091	Approved
0.7946	Intermediate Similarity	NPD5951	Approved
0.7863	Intermediate Similarity	NPD3092	Approved
0.7845	Intermediate Similarity	NPD7725	Approved
0.7845	Intermediate Similarity	NPD3095	Discontinued
0.7798	Intermediate Similarity	NPD2342	Discontinued
0.7768	Intermediate Similarity	NPD7635	Approved
0.7719	Intermediate Similarity	NPD4198	Discontinued
0.7692	Intermediate Similarity	NPD4059	Approved
0.7642	Intermediate Similarity	NPD3020	Approved
0.7603	Intermediate Similarity	NPD3094	Phase 2
0.7542	Intermediate Similarity	NPD5126	Approved
0.7542	Intermediate Similarity	NPD3019	Approved
0.7542	Intermediate Similarity	NPD5125	Phase 3
0.7542	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2227	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD845	Approved
0.7478	Intermediate Similarity	NPD2629	Approved
0.7474	Intermediate Similarity	NPD9294	Approved
0.7429	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6049	Phase 2
0.7429	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1616	Discontinued
0.7395	Intermediate Similarity	NPD2932	Approved
0.736	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7008	Discontinued
0.7358	Intermediate Similarity	NPD2860	Approved
0.7358	Intermediate Similarity	NPD1809	Phase 2
0.7358	Intermediate Similarity	NPD2859	Approved
0.735	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4817	Approved
0.7339	Intermediate Similarity	NPD5736	Approved
0.7339	Intermediate Similarity	NPD4818	Approved
0.7311	Intermediate Similarity	NPD1710	Approved
0.729	Intermediate Similarity	NPD288	Approved
0.7281	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4229	Approved
0.7273	Intermediate Similarity	NPD4231	Approved
0.7264	Intermediate Similarity	NPD2934	Approved
0.7264	Intermediate Similarity	NPD2933	Approved
0.7258	Intermediate Similarity	NPD4624	Approved
0.725	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6775	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD844	Approved
0.7168	Intermediate Similarity	NPD4095	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4658	Approved
0.7117	Intermediate Similarity	NPD3682	Approved
0.7117	Intermediate Similarity	NPD3680	Approved
0.7117	Intermediate Similarity	NPD4656	Approved
0.7109	Intermediate Similarity	NPD6663	Approved
0.7109	Intermediate Similarity	NPD7714	Approved
0.7109	Intermediate Similarity	NPD7715	Approved
0.7107	Intermediate Similarity	NPD2286	Discontinued
0.7105	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4097	Suspended
0.7075	Intermediate Similarity	NPD1088	Approved
0.7069	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4140	Approved
0.7054	Intermediate Similarity	NPD3620	Phase 2
0.7054	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3023	Approved
0.7049	Intermediate Similarity	NPD3026	Approved
0.7043	Intermediate Similarity	NPD3021	Approved
0.7043	Intermediate Similarity	NPD4750	Phase 3
0.7043	Intermediate Similarity	NPD3022	Approved
0.7027	Intermediate Similarity	NPD4719	Phase 2
0.7025	Intermediate Similarity	NPD3024	Approved
0.7025	Intermediate Similarity	NPD3025	Approved
0.7025	Intermediate Similarity	NPD4093	Discontinued
0.7019	Intermediate Similarity	NPD1101	Approved
0.7016	Intermediate Similarity	NPD5327	Phase 3
0.7	Intermediate Similarity	NPD5735	Approved
0.7	Intermediate Similarity	NPD2066	Phase 3
0.6984	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4253	Approved
0.6983	Remote Similarity	NPD4254	Approved
0.6975	Remote Similarity	NPD3317	Approved
0.697	Remote Similarity	NPD7743	Approved
0.697	Remote Similarity	NPD7742	Approved
0.6967	Remote Similarity	NPD1751	Approved
0.6964	Remote Similarity	NPD3683	Approved
0.6964	Remote Similarity	NPD3681	Approved
0.6949	Remote Similarity	NPD2229	Approved
0.6949	Remote Similarity	NPD2234	Approved
0.6949	Remote Similarity	NPD2228	Approved
0.6949	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6353	Approved
0.6944	Remote Similarity	NPD4814	Discontinued
0.6944	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1237	Approved
0.6903	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3046	Approved
0.6903	Remote Similarity	NPD3048	Approved
0.6903	Remote Similarity	NPD3047	Approved
0.6899	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1792	Phase 2
0.6893	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1086	Approved
0.6887	Remote Similarity	NPD1090	Approved
0.6887	Remote Similarity	NPD1089	Approved
0.688	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2606	Approved
0.6875	Remote Similarity	NPD2605	Approved
0.6863	Remote Similarity	NPD3971	Phase 1
0.686	Remote Similarity	NPD7610	Discontinued
0.6852	Remote Similarity	NPD3719	Approved
0.6852	Remote Similarity	NPD3718	Approved
0.6829	Remote Similarity	NPD4626	Approved
0.6822	Remote Similarity	NPD5155	Approved
0.6822	Remote Similarity	NPD5156	Approved
0.6822	Remote Similarity	NPD4625	Phase 3
0.6818	Remote Similarity	NPD3495	Discontinued
0.6814	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD1930	Approved
0.6814	Remote Similarity	NPD1929	Approved
0.681	Remote Similarity	NPD4718	Approved
0.681	Remote Similarity	NPD4717	Approved
0.681	Remote Similarity	NPD4720	Approved
0.6807	Remote Similarity	NPD6010	Discontinued
0.6803	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7250	Approved
0.68	Remote Similarity	NPD7249	Approved
0.6797	Remote Similarity	NPD3637	Approved
0.6797	Remote Similarity	NPD3635	Approved
0.6797	Remote Similarity	NPD3636	Approved
0.6792	Remote Similarity	NPD800	Approved
0.6789	Remote Similarity	NPD3772	Phase 3
0.6789	Remote Similarity	NPD1693	Approved
0.6777	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3897	Approved
0.6774	Remote Similarity	NPD3898	Approved
0.6774	Remote Similarity	NPD3895	Approved
0.6774	Remote Similarity	NPD3896	Approved
0.6765	Remote Similarity	NPD3638	Discontinued
0.6759	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD9495	Approved
0.6757	Remote Similarity	NPD9611	Approved
0.6757	Remote Similarity	NPD9609	Approved
0.6757	Remote Similarity	NPD9612	Approved
0.675	Remote Similarity	NPD497	Approved
0.6746	Remote Similarity	NPD6025	Phase 1
0.6744	Remote Similarity	NPD3594	Approved
0.6744	Remote Similarity	NPD3595	Approved
0.6727	Remote Similarity	NPD1989	Approved
0.6726	Remote Similarity	NPD855	Approved
0.6726	Remote Similarity	NPD854	Approved
0.6723	Remote Similarity	NPD7094	Approved
0.6723	Remote Similarity	NPD6858	Approved
0.6719	Remote Similarity	NPD2195	Approved
0.6719	Remote Similarity	NPD2194	Approved
0.6716	Remote Similarity	NPD6587	Approved
0.6716	Remote Similarity	NPD6586	Approved
0.6715	Remote Similarity	NPD7003	Approved
0.6697	Remote Similarity	NPD1409	Phase 3
0.6694	Remote Similarity	NPD7157	Approved
0.6694	Remote Similarity	NPD5305	Approved
0.6694	Remote Similarity	NPD5306	Approved
0.6694	Remote Similarity	NPD4589	Approved
0.6694	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6696	Suspended
0.6693	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD1564	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD1239	Approved
0.6667	Remote Similarity	NPD1565	Approved
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2230	Approved
0.6667	Remote Similarity	NPD1875	Phase 1
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD496	Approved
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD7330	Discontinued
0.6667	Remote Similarity	NPD2232	Approved
0.6667	Remote Similarity	NPD495	Approved
0.6667	Remote Similarity	NPD1566	Phase 3
0.6667	Remote Similarity	NPD2233	Approved
0.6667	Remote Similarity	NPD498	Approved
0.6642	Remote Similarity	NPD41	Approved
0.6642	Remote Similarity	NPD5886	Approved
0.6641	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2500	Approved
0.6639	Remote Similarity	NPD2499	Approved
0.6639	Remote Similarity	NPD7340	Approved
0.6638	Remote Similarity	NPD1445	Approved
0.6638	Remote Similarity	NPD1444	Approved
0.6637	Remote Similarity	NPD2552	Approved
0.6637	Remote Similarity	NPD2555	Approved
0.6637	Remote Similarity	NPD2553	Approved
0.6637	Remote Similarity	NPD2549	Approved
0.6637	Remote Similarity	NPD2550	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