NPASS Compound

Structure

CID172219 OpenBabel06191715542D 22 24 0 0 1 0 0 0 0 0999 V2000 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 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 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 1.7321 -1.0000 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 -0.8660 0.5000 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 0.8660 1.5000 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 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 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.79
LogD:	4.222
LogS:	-4.597
# 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:	0.843
Synthetic Accessibility Score:	3.653
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.66
MDCK Permeability:	1.3947195839136839e-05
Pgp-inhibitor:	0.513
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.598
Plasma Protein Binding (PPB):	97.86748504638672%
Volume Distribution (VD):	2.436
Pgp-substrate:	2.244478702545166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.267
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.28
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.659
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	7.699
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.91
Carcinogencity:	0.047
Eye Corrosion:	0.008
Eye Irritation:	0.933
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC172219

Natural Product ID:	NPC172219
*Common Name:**	Pisiferol
IUPAC Name:	(4bR,8aS)-4b-(hydroxymethyl)-8,8-dimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
Synonyms:	Pisiferol
Standard InCHIKey:	NKGGFTFDYGTUSL-ICSRJNTNSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)15-10-14-6-7-18-19(3,4)8-5-9-20(18,12-21)16(14)11-17(15)22/h10-11,13,18,21-22H,5-9,12H2,1-4H3/t18-,20-/m0/s1
SMILES:	OC[C@@]12CCCC([C@@H]2CCc2c1cc(O)c(c2)C(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL193987
PubChem CID:	185553
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
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	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
ED50	1
GI50	6
IC50	5

Activity Type	# Activity
Cell Line	11
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT323	Cell Line	SW-620	Homo sapiens	GI50	=	8.22	ug.mL-1	PMID[502856]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	4.34	ug.mL-1	PMID[502856]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	8.34	ug.mL-1	PMID[502856]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	2.8	ug.mL-1	PMID[502856]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	2.9	ug.mL-1	PMID[502856]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	100.0	ug ml-1	PMID[502857]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[502858]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[502858]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[502858]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[502858]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[502858]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	GI50	=	2.3	ug.mL-1	PMID[502856]

☑ 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 NPC172219 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	281
0.1-0.2	1490
0.2-0.3	3084
0.3-0.4	8908
0.4-0.5	10597
0.5-0.6	9205
0.6-0.7	7197
0.7-0.8	1650
0.8-0.85	168
0.85-0.9	81
0.9-0.95	19
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304510
0.9909	High Similarity	NPC471671
0.982	High Similarity	NPC469644
0.9817	High Similarity	NPC192948
0.9817	High Similarity	NPC35797
0.9727	High Similarity	NPC38893
0.9727	High Similarity	NPC477137
0.9727	High Similarity	NPC308311
0.9554	High Similarity	NPC469609
0.9554	High Similarity	NPC154030
0.955	High Similarity	NPC219112
0.9545	High Similarity	NPC268160
0.9464	High Similarity	NPC477136
0.9459	High Similarity	NPC147179
0.945	High Similarity	NPC176279
0.945	High Similarity	NPC260323
0.9375	High Similarity	NPC92
0.9375	High Similarity	NPC308828
0.9375	High Similarity	NPC469663
0.9204	High Similarity	NPC471668
0.9196	High Similarity	NPC195922
0.9189	High Similarity	NPC250323
0.9182	High Similarity	NPC141782
0.9182	High Similarity	NPC132720
0.916	High Similarity	NPC321822
0.916	High Similarity	NPC325294
0.9145	High Similarity	NPC471794
0.9138	High Similarity	NPC328504
0.9099	High Similarity	NPC151537
0.9083	High Similarity	NPC471077
0.9083	High Similarity	NPC151477
0.9068	High Similarity	NPC471187
0.9018	High Similarity	NPC46940
0.9018	High Similarity	NPC228425
0.9009	High Similarity	NPC13482
0.9	High Similarity	NPC43000
0.9	High Similarity	NPC100414
0.8992	High Similarity	NPC181334
0.8983	High Similarity	NPC71094
0.8983	High Similarity	NPC11250
0.8966	High Similarity	NPC126002
0.8966	High Similarity	NPC93071
0.8938	High Similarity	NPC715
0.8929	High Similarity	NPC95716
0.8926	High Similarity	NPC108164
0.8917	High Similarity	NPC87985
0.8917	High Similarity	NPC124030
0.8899	High Similarity	NPC117115
0.8889	High Similarity	NPC135467
0.8889	High Similarity	NPC260832
0.8879	High Similarity	NPC206
0.8879	High Similarity	NPC164649
0.8879	High Similarity	NPC48342
0.887	High Similarity	NPC141001
0.886	High Similarity	NPC471534
0.8829	High Similarity	NPC149455
0.8829	High Similarity	NPC11554
0.8829	High Similarity	NPC64642
0.8829	High Similarity	NPC472982
0.8818	High Similarity	NPC21594
0.8803	High Similarity	NPC151197
0.8793	High Similarity	NPC16030
0.8783	High Similarity	NPC469719
0.877	High Similarity	NPC186889
0.877	High Similarity	NPC476536
0.8761	High Similarity	NPC77772
0.8761	High Similarity	NPC322753
0.876	High Similarity	NPC137750
0.875	High Similarity	NPC58865
0.875	High Similarity	NPC198014
0.8739	High Similarity	NPC253627
0.8739	High Similarity	NPC77569
0.8739	High Similarity	NPC249340
0.8739	High Similarity	NPC142198
0.8739	High Similarity	NPC162935
0.8729	High Similarity	NPC68339
0.8707	High Similarity	NPC257540
0.8707	High Similarity	NPC137496
0.8707	High Similarity	NPC247858
0.8707	High Similarity	NPC474387
0.8707	High Similarity	NPC474358
0.8707	High Similarity	NPC154511
0.8667	High Similarity	NPC152946
0.8655	High Similarity	NPC32322
0.8655	High Similarity	NPC259703
0.864	High Similarity	NPC312341
0.8621	High Similarity	NPC246760
0.8621	High Similarity	NPC84999
0.8609	High Similarity	NPC263753
0.8609	High Similarity	NPC317869
0.8607	High Similarity	NPC4286
0.8607	High Similarity	NPC76119
0.8596	High Similarity	NPC470770
0.8596	High Similarity	NPC469912
0.8596	High Similarity	NPC266937
0.8584	High Similarity	NPC314187
0.8583	High Similarity	NPC154696
0.8583	High Similarity	NPC475166
0.8571	High Similarity	NPC321086
0.8571	High Similarity	NPC472979
0.8571	High Similarity	NPC27252
0.856	High Similarity	NPC196193
0.8559	High Similarity	NPC219286
0.8559	High Similarity	NPC99557
0.8559	High Similarity	NPC243601
0.8534	High Similarity	NPC249270
0.8534	High Similarity	NPC107240
0.8532	High Similarity	NPC211885
0.8522	High Similarity	NPC62867
0.8522	High Similarity	NPC473521
0.8522	High Similarity	NPC302371
0.8522	High Similarity	NPC177962
0.8522	High Similarity	NPC471179
0.8512	High Similarity	NPC176208
0.8512	High Similarity	NPC478058
0.8512	High Similarity	NPC321402
0.8512	High Similarity	NPC121168
0.8509	High Similarity	NPC224870
0.8504	High Similarity	NPC49742
0.8504	High Similarity	NPC227719
0.85	High Similarity	NPC241001
0.8492	Intermediate Similarity	NPC476847
0.8492	Intermediate Similarity	NPC471851
0.8487	Intermediate Similarity	NPC176893
0.8482	Intermediate Similarity	NPC271274
0.8475	Intermediate Similarity	NPC299180
0.8468	Intermediate Similarity	NPC475225
0.8448	Intermediate Similarity	NPC319803
0.8448	Intermediate Similarity	NPC117846
0.8448	Intermediate Similarity	NPC322239
0.8425	Intermediate Similarity	NPC165612
0.8425	Intermediate Similarity	NPC59239
0.8417	Intermediate Similarity	NPC478121
0.8413	Intermediate Similarity	NPC99795
0.8407	Intermediate Similarity	NPC320439
0.8407	Intermediate Similarity	NPC472980
0.84	Intermediate Similarity	NPC223912
0.8387	Intermediate Similarity	NPC470724
0.8387	Intermediate Similarity	NPC71610
0.8378	Intermediate Similarity	NPC235762
0.8378	Intermediate Similarity	NPC471228
0.8378	Intermediate Similarity	NPC19856
0.8376	Intermediate Similarity	NPC12656
0.8374	Intermediate Similarity	NPC224342
0.8364	Intermediate Similarity	NPC225506
0.8361	Intermediate Similarity	NPC297057
0.8359	Intermediate Similarity	NPC78307
0.8348	Intermediate Similarity	NPC296683
0.8346	Intermediate Similarity	NPC78575
0.8333	Intermediate Similarity	NPC262365
0.8333	Intermediate Similarity	NPC42657
0.8333	Intermediate Similarity	NPC323074
0.832	Intermediate Similarity	NPC78364
0.832	Intermediate Similarity	NPC176130
0.832	Intermediate Similarity	NPC69424
0.832	Intermediate Similarity	NPC84672
0.8308	Intermediate Similarity	NPC68292
0.8306	Intermediate Similarity	NPC470726
0.8305	Intermediate Similarity	NPC474486
0.8304	Intermediate Similarity	NPC238696
0.8304	Intermediate Similarity	NPC272029
0.8295	Intermediate Similarity	NPC202225
0.8288	Intermediate Similarity	NPC252105
0.8281	Intermediate Similarity	NPC85595
0.8279	Intermediate Similarity	NPC474115
0.8276	Intermediate Similarity	NPC476632
0.8276	Intermediate Similarity	NPC165770
0.8276	Intermediate Similarity	NPC4493
0.8276	Intermediate Similarity	NPC224527
0.8276	Intermediate Similarity	NPC225679
0.8273	Intermediate Similarity	NPC122005
0.8273	Intermediate Similarity	NPC128723
0.8273	Intermediate Similarity	NPC252821
0.8273	Intermediate Similarity	NPC299762
0.8273	Intermediate Similarity	NPC33675
0.8268	Intermediate Similarity	NPC249425
0.8268	Intermediate Similarity	NPC472793
0.8264	Intermediate Similarity	NPC103916
0.8264	Intermediate Similarity	NPC318581
0.8264	Intermediate Similarity	NPC318552
0.8264	Intermediate Similarity	NPC477037
0.8264	Intermediate Similarity	NPC325544
0.8264	Intermediate Similarity	NPC190501
0.8264	Intermediate Similarity	NPC99734
0.8261	Intermediate Similarity	NPC299568
0.8261	Intermediate Similarity	NPC186385
0.8254	Intermediate Similarity	NPC201069
0.8254	Intermediate Similarity	NPC3009
0.825	Intermediate Similarity	NPC48781
0.825	Intermediate Similarity	NPC9592
0.8246	Intermediate Similarity	NPC66834
0.8235	Intermediate Similarity	NPC312105
0.8235	Intermediate Similarity	NPC115808
0.8235	Intermediate Similarity	NPC472862
0.823	Intermediate Similarity	NPC47284
0.823	Intermediate Similarity	NPC138942
0.823	Intermediate Similarity	NPC471350
0.822	Intermediate Similarity	NPC473137
0.8217	Intermediate Similarity	NPC477139
0.8214	Intermediate Similarity	NPC168829

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 NPC172219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	918
0.2-0.3	1376
0.3-0.4	2872
0.4-0.5	1960
0.5-0.6	1223
0.6-0.7	418
0.7-0.8	95
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8879	High Similarity	NPD3091	Approved
0.8739	High Similarity	NPD3092	Approved
0.8455	Intermediate Similarity	NPD3094	Phase 2
0.8417	Intermediate Similarity	NPD3095	Discontinued
0.8407	Intermediate Similarity	NPD2342	Discontinued
0.8362	Intermediate Similarity	NPD7635	Approved
0.8264	Intermediate Similarity	NPD3019	Approved
0.8264	Intermediate Similarity	NPD4059	Approved
0.8261	Intermediate Similarity	NPD4750	Phase 3
0.8165	Intermediate Similarity	NPD1809	Phase 2
0.8115	Intermediate Similarity	NPD2932	Approved
0.8108	Intermediate Similarity	NPD3020	Approved
0.8091	Intermediate Similarity	NPD288	Approved
0.8031	Intermediate Similarity	NPD5736	Approved
0.8	Intermediate Similarity	NPD844	Approved
0.7953	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4097	Suspended
0.7876	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD3620	Phase 2
0.7857	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2859	Approved
0.7838	Intermediate Similarity	NPD2860	Approved
0.7823	Intermediate Similarity	NPD2286	Discontinued
0.7818	Intermediate Similarity	NPD845	Approved
0.7815	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD3022	Approved
0.7797	Intermediate Similarity	NPD3021	Approved
0.7786	Intermediate Similarity	NPD6663	Approved
0.7748	Intermediate Similarity	NPD2933	Approved
0.7748	Intermediate Similarity	NPD2934	Approved
0.7742	Intermediate Similarity	NPD4093	Discontinued
0.7686	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD4626	Approved
0.768	Intermediate Similarity	NPD1751	Approved
0.7674	Intermediate Similarity	NPD4624	Approved
0.7669	Intermediate Similarity	NPD5735	Approved
0.7656	Intermediate Similarity	NPD6696	Suspended
0.7652	Intermediate Similarity	NPD940	Approved
0.7652	Intermediate Similarity	NPD846	Approved
0.7634	Intermediate Similarity	NPD4625	Phase 3
0.763	Intermediate Similarity	NPD7742	Approved
0.763	Intermediate Similarity	NPD7743	Approved
0.7619	Intermediate Similarity	NPD3026	Approved
0.7619	Intermediate Similarity	NPD3023	Approved
0.76	Intermediate Similarity	NPD3025	Approved
0.76	Intermediate Similarity	NPD3024	Approved
0.7594	Intermediate Similarity	NPD4140	Approved
0.7586	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5327	Phase 3
0.7576	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD1201	Approved
0.7557	Intermediate Similarity	NPD2606	Approved
0.7557	Intermediate Similarity	NPD2605	Approved
0.7541	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5156	Approved
0.75	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5155	Approved
0.7481	Intermediate Similarity	NPD3636	Approved
0.7481	Intermediate Similarity	NPD3637	Approved
0.7481	Intermediate Similarity	NPD2861	Phase 2
0.7481	Intermediate Similarity	NPD3635	Approved
0.7463	Intermediate Similarity	NPD4060	Phase 1
0.7462	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5691	Approved
0.7442	Intermediate Similarity	NPD4749	Approved
0.7424	Intermediate Similarity	NPD3595	Approved
0.7424	Intermediate Similarity	NPD4908	Phase 1
0.7424	Intermediate Similarity	NPD3594	Approved
0.7414	Intermediate Similarity	NPD1242	Phase 1
0.741	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3638	Discontinued
0.7405	Intermediate Similarity	NPD2195	Approved
0.7405	Intermediate Similarity	NPD2194	Approved
0.7402	Intermediate Similarity	NPD4589	Approved
0.7402	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4725	Approved
0.7391	Intermediate Similarity	NPD4726	Approved
0.7391	Intermediate Similarity	NPD4721	Approved
0.7372	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1792	Phase 2
0.7353	Intermediate Similarity	NPD6353	Approved
0.7339	Intermediate Similarity	NPD497	Approved
0.7328	Intermediate Similarity	NPD1470	Approved
0.7319	Intermediate Similarity	NPD5404	Approved
0.7319	Intermediate Similarity	NPD5406	Approved
0.7319	Intermediate Similarity	NPD5405	Approved
0.7319	Intermediate Similarity	NPD5408	Approved
0.7305	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2229	Approved
0.7258	Intermediate Similarity	NPD495	Approved
0.7258	Intermediate Similarity	NPD498	Approved
0.7258	Intermediate Similarity	NPD2234	Approved
0.7258	Intermediate Similarity	NPD496	Approved
0.7258	Intermediate Similarity	NPD2228	Approved
0.7252	Intermediate Similarity	NPD8651	Approved
0.7252	Intermediate Similarity	NPD1283	Approved
0.7244	Intermediate Similarity	NPD5303	Approved
0.7244	Intermediate Similarity	NPD5304	Approved
0.7244	Intermediate Similarity	NPD7741	Discontinued
0.7234	Intermediate Similarity	NPD7003	Approved
0.7222	Intermediate Similarity	NPD7340	Approved
0.7203	Intermediate Similarity	NPD7390	Discontinued
0.7194	Intermediate Similarity	NPD6100	Approved
0.7194	Intermediate Similarity	NPD6099	Approved
0.7188	Intermediate Similarity	NPD1651	Approved
0.7176	Intermediate Similarity	NPD4659	Approved
0.7163	Intermediate Similarity	NPD6674	Discontinued
0.7153	Intermediate Similarity	NPD3645	Discontinued
0.712	Intermediate Similarity	NPD1398	Phase 1
0.7113	Intermediate Similarity	NPD8166	Discontinued
0.7109	Intermediate Similarity	NPD7330	Discontinued
0.7109	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1445	Approved
0.7107	Intermediate Similarity	NPD1444	Approved
0.7091	Intermediate Similarity	NPD111	Approved
0.7083	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7041	Phase 2
0.708	Intermediate Similarity	NPD2238	Phase 2
0.7068	Intermediate Similarity	NPD4103	Phase 2
0.7068	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3657	Discovery
0.7023	Intermediate Similarity	NPD1281	Approved
0.7021	Intermediate Similarity	NPD5763	Approved
0.7021	Intermediate Similarity	NPD5762	Approved
0.7021	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6584	Phase 3
0.7008	Intermediate Similarity	NPD7157	Approved
0.7008	Intermediate Similarity	NPD6671	Approved
0.7007	Intermediate Similarity	NPD6407	Approved
0.7007	Intermediate Similarity	NPD6405	Approved
0.7	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3027	Phase 3
0.6984	Remote Similarity	NPD5283	Phase 1
0.6977	Remote Similarity	NPD1548	Phase 1
0.6972	Remote Similarity	NPD7037	Approved
0.697	Remote Similarity	NPD2232	Approved
0.697	Remote Similarity	NPD2233	Approved
0.697	Remote Similarity	NPD2230	Approved
0.6963	Remote Similarity	NPD4208	Discontinued
0.6947	Remote Similarity	NPD3143	Discontinued
0.6944	Remote Similarity	NPD8131	Suspended
0.694	Remote Similarity	NPD1135	Approved
0.694	Remote Similarity	NPD1131	Approved
0.694	Remote Similarity	NPD1129	Approved
0.694	Remote Similarity	NPD1133	Approved
0.694	Remote Similarity	NPD1134	Approved
0.6935	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5951	Approved
0.6929	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1669	Approved
0.6884	Remote Similarity	NPD8032	Phase 2
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6273	Approved
0.687	Remote Similarity	NPD5125	Phase 3
0.687	Remote Similarity	NPD5126	Approved
0.687	Remote Similarity	NPD1778	Approved
0.686	Remote Similarity	NPD9500	Approved
0.6857	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2157	Approved
0.6855	Remote Similarity	NPD2684	Approved
0.6849	Remote Similarity	NPD2421	Approved
0.6849	Remote Similarity	NPD2420	Approved
0.6842	Remote Similarity	NPD2561	Approved
0.6842	Remote Similarity	NPD2562	Approved
0.6842	Remote Similarity	NPD3070	Discontinued
0.6835	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3110	Approved
0.6835	Remote Similarity	NPD3109	Approved
0.6835	Remote Similarity	NPD2979	Phase 3
0.6835	Remote Similarity	NPD1613	Approved
0.6833	Remote Similarity	NPD3028	Approved
0.6825	Remote Similarity	NPD228	Approved
0.6824	Remote Similarity	NPD5699	Approved
0.6822	Remote Similarity	NPD7636	Approved
0.6821	Remote Similarity	NPD37	Approved
0.6818	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7294	Phase 1
0.6809	Remote Similarity	NPD3552	Approved
0.6809	Remote Similarity	NPD3554	Approved
0.6809	Remote Similarity	NPD3555	Approved
0.6809	Remote Similarity	NPD3553	Approved
0.68	Remote Similarity	NPD5451	Approved
0.6797	Remote Similarity	NPD1791	Approved
0.6797	Remote Similarity	NPD1793	Approved
0.6791	Remote Similarity	NPD6583	Phase 3
0.6791	Remote Similarity	NPD6582	Phase 2
0.6769	Remote Similarity	NPD856	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