NPASS Compound

Structure

CID154030 OpenBabel06191715522D 21 23 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 4.3301 -1.5000 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 -2.2321 -0.8660 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 -0.8660 -1.5000 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 -1.7321 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 1.7321 -0.0000 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 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 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 0.0000 0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 1 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.19
Volume:	318.545
LogP:	4.665
LogD:	4.106
LogS:	-4.619
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	3.49
Fsp3:	0.579
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:	-5.013
MDCK Permeability:	1.9542638256098144e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.521
Plasma Protein Binding (PPB):	97.66376495361328%
Volume Distribution (VD):	2.106
Pgp-substrate:	2.2307536602020264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.714
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.401
CYP2C19-substrate:	0.5
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.887
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.425

ADMET: Excretion

Clearance (CL):	1.971
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.4
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.705
Carcinogencity:	0.047
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC154030

Natural Product ID:	NPC154030
*Common Name:**	(+)-(1R)-1,12-Dihydroxy-20-Norabieta-5(10),8,11,13-Tetraene
IUPAC Name:	(5R)-8,8-dimethyl-2-propan-2-yl-6,7,9,10-tetrahydro-5H-phenanthrene-3,5-diol
Synonyms:
Standard InCHIKey:	VGYQUIDVXNWOOS-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C19H26O2/c1-11(2)13-9-12-5-6-15-18(14(12)10-17(13)21)16(20)7-8-19(15,3)4/h9-11,16,20-21H,5-8H2,1-4H3/t16-/m1/s1
SMILES:	CC(C)c1cc2CCC3=C(c2cc1O)[C@@H](CCC3(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651074
PubChem CID:	50900600
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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[473695]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[473695]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[473695]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[473695]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[473695]

☑ 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 NPC154030 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	304
0.1-0.2	1487
0.2-0.3	3105
0.3-0.4	9633
0.4-0.5	10132
0.5-0.6	9483
0.6-0.7	6706
0.7-0.8	1585
0.8-0.85	186
0.85-0.9	49
0.9-0.95	22
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC471671
0.9558	High Similarity	NPC469644
0.9554	High Similarity	NPC304510
0.9554	High Similarity	NPC477136
0.9554	High Similarity	NPC172219
0.9464	High Similarity	NPC308311
0.9464	High Similarity	NPC38893
0.9464	High Similarity	NPC477137
0.9375	High Similarity	NPC192948
0.9375	High Similarity	NPC35797
0.9298	High Similarity	NPC469609
0.9292	High Similarity	NPC219112
0.9204	High Similarity	NPC147179
0.9123	High Similarity	NPC92
0.9123	High Similarity	NPC308828
0.9123	High Similarity	NPC469663
0.9115	High Similarity	NPC268160
0.9107	High Similarity	NPC250323
0.9018	High Similarity	NPC176279
0.9018	High Similarity	NPC260323
0.8957	High Similarity	NPC471668
0.8938	High Similarity	NPC228425
0.8929	High Similarity	NPC132720
0.8929	High Similarity	NPC13482
0.8909	High Similarity	NPC21594
0.8908	High Similarity	NPC471794
0.8898	High Similarity	NPC328504
0.8852	High Similarity	NPC471077
0.885	High Similarity	NPC151537
0.8843	High Similarity	NPC124030
0.8829	High Similarity	NPC151477
0.8783	High Similarity	NPC195922
0.877	High Similarity	NPC321822
0.877	High Similarity	NPC325294
0.8761	High Similarity	NPC141782
0.876	High Similarity	NPC181334
0.875	High Similarity	NPC152946
0.875	High Similarity	NPC71094
0.8729	High Similarity	NPC93071
0.8696	High Similarity	NPC319803
0.8689	High Similarity	NPC87985
0.8689	High Similarity	NPC4286
0.8689	High Similarity	NPC76119
0.8678	High Similarity	NPC471187
0.8655	High Similarity	NPC135467
0.8655	High Similarity	NPC68339
0.8655	High Similarity	NPC260832
0.8649	High Similarity	NPC117115
0.8644	High Similarity	NPC164649
0.8644	High Similarity	NPC48342
0.8632	High Similarity	NPC474358
0.8632	High Similarity	NPC137496
0.8632	High Similarity	NPC154511
0.8632	High Similarity	NPC247858
0.8632	High Similarity	NPC257540
0.8632	High Similarity	NPC474387
0.8618	High Similarity	NPC100414
0.8618	High Similarity	NPC43000
0.8609	High Similarity	NPC46940
0.8609	High Similarity	NPC473521
0.8595	High Similarity	NPC11250
0.8584	High Similarity	NPC472982
0.8584	High Similarity	NPC149455
0.8584	High Similarity	NPC64642
0.8583	High Similarity	NPC259703
0.8583	High Similarity	NPC32322
0.8571	High Similarity	NPC151197
0.8571	High Similarity	NPC126002
0.8548	High Similarity	NPC108164
0.8548	High Similarity	NPC186889
0.8537	High Similarity	NPC470726
0.8534	High Similarity	NPC715
0.8534	High Similarity	NPC263753
0.8522	High Similarity	NPC266937
0.8522	High Similarity	NPC469912
0.8522	High Similarity	NPC95716
0.8522	High Similarity	NPC470770
0.8512	High Similarity	NPC154696
0.8512	High Similarity	NPC77569
0.8512	High Similarity	NPC142198
0.8509	High Similarity	NPC58865
0.8504	High Similarity	NPC165612
0.8496	Intermediate Similarity	NPC472980
0.8487	Intermediate Similarity	NPC206
0.8475	Intermediate Similarity	NPC141001
0.8462	Intermediate Similarity	NPC471534
0.8455	Intermediate Similarity	NPC211885
0.8448	Intermediate Similarity	NPC177962
0.8448	Intermediate Similarity	NPC62867
0.8448	Intermediate Similarity	NPC302371
0.8443	Intermediate Similarity	NPC478058
0.8435	Intermediate Similarity	NPC224870
0.8425	Intermediate Similarity	NPC312341
0.8421	Intermediate Similarity	NPC11554
0.8403	Intermediate Similarity	NPC16030
0.84	Intermediate Similarity	NPC476536
0.8393	Intermediate Similarity	NPC475225
0.839	Intermediate Similarity	NPC474486
0.839	Intermediate Similarity	NPC469719
0.8387	Intermediate Similarity	NPC137750
0.8374	Intermediate Similarity	NPC198014
0.8362	Intermediate Similarity	NPC322753
0.8362	Intermediate Similarity	NPC77772
0.8361	Intermediate Similarity	NPC474115
0.8361	Intermediate Similarity	NPC475166
0.8361	Intermediate Similarity	NPC253627
0.8361	Intermediate Similarity	NPC162935
0.8361	Intermediate Similarity	NPC249340
0.8359	Intermediate Similarity	NPC321086
0.8359	Intermediate Similarity	NPC59239
0.8348	Intermediate Similarity	NPC186385
0.8348	Intermediate Similarity	NPC299568
0.8347	Intermediate Similarity	NPC325544
0.8347	Intermediate Similarity	NPC477037
0.8347	Intermediate Similarity	NPC318581
0.8346	Intermediate Similarity	NPC196193
0.8346	Intermediate Similarity	NPC99795
0.8333	Intermediate Similarity	NPC27252
0.8333	Intermediate Similarity	NPC472979
0.832	Intermediate Similarity	NPC71610
0.832	Intermediate Similarity	NPC470724
0.8319	Intermediate Similarity	NPC219286
0.8319	Intermediate Similarity	NPC471350
0.8319	Intermediate Similarity	NPC99557
0.8319	Intermediate Similarity	NPC243601
0.8305	Intermediate Similarity	NPC107240
0.8305	Intermediate Similarity	NPC12656
0.8304	Intermediate Similarity	NPC471228
0.8304	Intermediate Similarity	NPC235762
0.8295	Intermediate Similarity	NPC227719
0.8293	Intermediate Similarity	NPC121168
0.8293	Intermediate Similarity	NPC321402
0.8291	Intermediate Similarity	NPC471179
0.8288	Intermediate Similarity	NPC225506
0.8281	Intermediate Similarity	NPC78575
0.8281	Intermediate Similarity	NPC476847
0.8279	Intermediate Similarity	NPC241001
0.8276	Intermediate Similarity	NPC296683
0.8261	Intermediate Similarity	NPC262365
0.825	Intermediate Similarity	NPC320864
0.8235	Intermediate Similarity	NPC84999
0.8235	Intermediate Similarity	NPC246760
0.823	Intermediate Similarity	NPC272029
0.822	Intermediate Similarity	NPC117846
0.822	Intermediate Similarity	NPC317869
0.8214	Intermediate Similarity	NPC252105
0.8205	Intermediate Similarity	NPC54373
0.8198	Intermediate Similarity	NPC128723
0.8198	Intermediate Similarity	NPC33675
0.8198	Intermediate Similarity	NPC252821
0.8198	Intermediate Similarity	NPC299762
0.8198	Intermediate Similarity	NPC122005
0.8197	Intermediate Similarity	NPC282255
0.8197	Intermediate Similarity	NPC3239
0.8197	Intermediate Similarity	NPC478121
0.819	Intermediate Similarity	NPC314187
0.8189	Intermediate Similarity	NPC223912
0.8182	Intermediate Similarity	NPC9592
0.8182	Intermediate Similarity	NPC48781
0.8174	Intermediate Similarity	NPC320439
0.8174	Intermediate Similarity	NPC66834
0.8167	Intermediate Similarity	NPC312105
0.8158	Intermediate Similarity	NPC47284
0.8154	Intermediate Similarity	NPC78307
0.8154	Intermediate Similarity	NPC49742
0.8151	Intermediate Similarity	NPC249270
0.8151	Intermediate Similarity	NPC473137
0.8145	Intermediate Similarity	NPC176208
0.8145	Intermediate Similarity	NPC297057
0.8142	Intermediate Similarity	NPC269212
0.814	Intermediate Similarity	NPC471851
0.8125	Intermediate Similarity	NPC72729
0.8125	Intermediate Similarity	NPC174911
0.812	Intermediate Similarity	NPC44732
0.8115	Intermediate Similarity	NPC323074
0.8115	Intermediate Similarity	NPC176893
0.811	Intermediate Similarity	NPC72667
0.8108	Intermediate Similarity	NPC79241
0.8108	Intermediate Similarity	NPC77492
0.8108	Intermediate Similarity	NPC6597
0.8106	Intermediate Similarity	NPC68292
0.8103	Intermediate Similarity	NPC306295
0.8099	Intermediate Similarity	NPC299180
0.8095	Intermediate Similarity	NPC293801
0.8091	Intermediate Similarity	NPC222146
0.8091	Intermediate Similarity	NPC144682
0.8087	Intermediate Similarity	NPC53740
0.8087	Intermediate Similarity	NPC469913
0.8087	Intermediate Similarity	NPC155072
0.8087	Intermediate Similarity	NPC271274
0.8077	Intermediate Similarity	NPC85595
0.807	Intermediate Similarity	NPC238696
0.8067	Intermediate Similarity	NPC322239
0.8062	Intermediate Similarity	NPC470727
0.8051	Intermediate Similarity	NPC224527
0.8051	Intermediate Similarity	NPC225679
0.8051	Intermediate Similarity	NPC470723
0.8051	Intermediate Similarity	NPC4493
0.8051	Intermediate Similarity	NPC165770
0.8051	Intermediate Similarity	NPC476632

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 NPC154030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	957
0.2-0.3	1520
0.3-0.4	2900
0.4-0.5	1858
0.5-0.6	1133
0.6-0.7	400
0.7-0.8	82
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8644	High Similarity	NPD3091	Approved
0.8512	High Similarity	NPD3092	Approved
0.8348	Intermediate Similarity	NPD4750	Phase 3
0.824	Intermediate Similarity	NPD3094	Phase 2
0.8197	Intermediate Similarity	NPD3095	Discontinued
0.8136	Intermediate Similarity	NPD7635	Approved
0.8091	Intermediate Similarity	NPD1809	Phase 2
0.8049	Intermediate Similarity	NPD2932	Approved
0.8031	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD288	Approved
0.8017	Intermediate Similarity	NPD2342	Discontinued
0.7928	Intermediate Similarity	NPD844	Approved
0.7923	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD3019	Approved
0.7903	Intermediate Similarity	NPD4059	Approved
0.7876	Intermediate Similarity	NPD3020	Approved
0.7838	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5736	Approved
0.7807	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD845	Approved
0.7669	Intermediate Similarity	NPD3620	Phase 2
0.7669	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4626	Approved
0.7611	Intermediate Similarity	NPD2859	Approved
0.7611	Intermediate Similarity	NPD2860	Approved
0.7597	Intermediate Similarity	NPD6696	Suspended
0.7594	Intermediate Similarity	NPD6663	Approved
0.7586	Intermediate Similarity	NPD846	Approved
0.7586	Intermediate Similarity	NPD940	Approved
0.7583	Intermediate Similarity	NPD3022	Approved
0.7583	Intermediate Similarity	NPD3021	Approved
0.7556	Intermediate Similarity	NPD4097	Suspended
0.7522	Intermediate Similarity	NPD2934	Approved
0.7522	Intermediate Similarity	NPD2933	Approved
0.7521	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5735	Approved
0.748	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD2286	Discontinued
0.748	Intermediate Similarity	NPD1751	Approved
0.7462	Intermediate Similarity	NPD8651	Approved
0.7445	Intermediate Similarity	NPD7743	Approved
0.7445	Intermediate Similarity	NPD7742	Approved
0.7444	Intermediate Similarity	NPD4625	Phase 3
0.7424	Intermediate Similarity	NPD2861	Phase 2
0.7407	Intermediate Similarity	NPD4140	Approved
0.7402	Intermediate Similarity	NPD4093	Discontinued
0.7402	Intermediate Similarity	NPD5691	Approved
0.7385	Intermediate Similarity	NPD5327	Phase 3
0.7357	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4624	Approved
0.7344	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3637	Approved
0.7293	Intermediate Similarity	NPD3635	Approved
0.7293	Intermediate Similarity	NPD3636	Approved
0.7287	Intermediate Similarity	NPD3023	Approved
0.7287	Intermediate Similarity	NPD3026	Approved
0.7279	Intermediate Similarity	NPD4060	Phase 1
0.7266	Intermediate Similarity	NPD3025	Approved
0.7266	Intermediate Similarity	NPD3024	Approved
0.7259	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2606	Approved
0.7239	Intermediate Similarity	NPD2605	Approved
0.7234	Intermediate Similarity	NPD3638	Discontinued
0.7231	Intermediate Similarity	NPD1201	Approved
0.7218	Intermediate Similarity	NPD2194	Approved
0.7218	Intermediate Similarity	NPD2195	Approved
0.7209	Intermediate Similarity	NPD4589	Approved
0.7203	Intermediate Similarity	NPD1242	Phase 1
0.7185	Intermediate Similarity	NPD5156	Approved
0.7185	Intermediate Similarity	NPD5155	Approved
0.7174	Intermediate Similarity	NPD6353	Approved
0.7165	Intermediate Similarity	NPD7340	Approved
0.7154	Intermediate Similarity	NPD1792	Phase 2
0.7143	Intermediate Similarity	NPD497	Approved
0.7143	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4659	Approved
0.7111	Intermediate Similarity	NPD3594	Approved
0.7111	Intermediate Similarity	NPD4908	Phase 1
0.7111	Intermediate Similarity	NPD3595	Approved
0.7103	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1610	Phase 2
0.7092	Intermediate Similarity	NPD4726	Approved
0.7092	Intermediate Similarity	NPD4725	Approved
0.7092	Intermediate Similarity	NPD4721	Approved
0.7071	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1283	Approved
0.7063	Intermediate Similarity	NPD495	Approved
0.7063	Intermediate Similarity	NPD1398	Phase 1
0.7063	Intermediate Similarity	NPD2234	Approved
0.7063	Intermediate Similarity	NPD498	Approved
0.7063	Intermediate Similarity	NPD2229	Approved
0.7063	Intermediate Similarity	NPD2228	Approved
0.7063	Intermediate Similarity	NPD496	Approved
0.7054	Intermediate Similarity	NPD5304	Approved
0.7054	Intermediate Similarity	NPD7741	Discontinued
0.7054	Intermediate Similarity	NPD5303	Approved
0.7049	Intermediate Similarity	NPD1444	Approved
0.7049	Intermediate Similarity	NPD1445	Approved
0.7031	Intermediate Similarity	NPD7636	Approved
0.7029	Intermediate Similarity	NPD2238	Phase 2
0.7027	Intermediate Similarity	NPD111	Approved
0.7021	Intermediate Similarity	NPD6100	Approved
0.7021	Intermediate Similarity	NPD5405	Approved
0.7021	Intermediate Similarity	NPD6099	Approved
0.7021	Intermediate Similarity	NPD5408	Approved
0.7021	Intermediate Similarity	NPD5406	Approved
0.7021	Intermediate Similarity	NPD5404	Approved
0.7016	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1134	Approved
0.7015	Intermediate Similarity	NPD4103	Phase 2
0.7015	Intermediate Similarity	NPD1131	Approved
0.7015	Intermediate Similarity	NPD1135	Approved
0.7015	Intermediate Similarity	NPD1129	Approved
0.7015	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1470	Approved
0.7015	Intermediate Similarity	NPD1133	Approved
0.7	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6674	Discontinued
0.6986	Remote Similarity	NPD3645	Discontinued
0.6972	Remote Similarity	NPD5762	Approved
0.6972	Remote Similarity	NPD5763	Approved
0.6972	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6407	Approved
0.6957	Remote Similarity	NPD6405	Approved
0.6953	Remote Similarity	NPD7157	Approved
0.6953	Remote Similarity	NPD6671	Approved
0.6944	Remote Similarity	NPD8166	Discontinued
0.6944	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7003	Approved
0.6934	Remote Similarity	NPD3027	Phase 3
0.6923	Remote Similarity	NPD7330	Discontinued
0.6923	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7041	Phase 2
0.6918	Remote Similarity	NPD7390	Discontinued
0.6918	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4208	Discontinued
0.6894	Remote Similarity	NPD3143	Discontinued
0.6857	Remote Similarity	NPD3657	Discovery
0.6846	Remote Similarity	NPD16	Approved
0.6846	Remote Similarity	NPD856	Approved
0.6842	Remote Similarity	NPD1281	Approved
0.6831	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5125	Phase 3
0.6818	Remote Similarity	NPD9384	Approved
0.6818	Remote Similarity	NPD1778	Approved
0.6818	Remote Similarity	NPD5126	Approved
0.6818	Remote Similarity	NPD9381	Approved
0.6809	Remote Similarity	NPD2157	Approved
0.6803	Remote Similarity	NPD9500	Approved
0.68	Remote Similarity	NPD2684	Approved
0.6797	Remote Similarity	NPD5283	Phase 1
0.6794	Remote Similarity	NPD1548	Phase 1
0.6791	Remote Similarity	NPD3070	Discontinued
0.6791	Remote Similarity	NPD2561	Approved
0.6791	Remote Similarity	NPD2233	Approved
0.6791	Remote Similarity	NPD2562	Approved
0.6791	Remote Similarity	NPD2232	Approved
0.6791	Remote Similarity	NPD2230	Approved
0.6786	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1613	Approved
0.6772	Remote Similarity	NPD2489	Approved
0.6772	Remote Similarity	NPD27	Approved
0.6772	Remote Similarity	NPD228	Approved
0.6769	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3552	Approved
0.6761	Remote Similarity	NPD3554	Approved
0.6761	Remote Similarity	NPD3553	Approved
0.6761	Remote Similarity	NPD3555	Approved
0.6757	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1791	Approved
0.6744	Remote Similarity	NPD9614	Approved
0.6744	Remote Similarity	NPD1793	Approved
0.6744	Remote Similarity	NPD9618	Approved
0.6744	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1357	Approved
0.6741	Remote Similarity	NPD9622	Approved
0.6741	Remote Similarity	NPD1669	Approved
0.6718	Remote Similarity	NPD317	Approved
0.6718	Remote Similarity	NPD318	Approved
0.6715	Remote Similarity	NPD6584	Phase 3
0.6711	Remote Similarity	NPD6273	Approved
0.6709	Remote Similarity	NPD2970	Approved
0.6709	Remote Similarity	NPD2969	Approved
0.669	Remote Similarity	NPD7037	Approved
0.6667	Remote Similarity	NPD5699	Approved
0.6667	Remote Similarity	NPD5709	Phase 3
0.6667	Remote Similarity	NPD8131	Suspended
0.6667	Remote Similarity	NPD37	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