NPASS Compound

Structure

NPC471189 OpenBabel07101718202D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 1.7321 -3.0000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 3 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 2.5981 -1.5000 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 -0.8660 -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 1 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 -0.0000 -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 1 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 14 15 2 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 19 1 0 0 0 0 18 23 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.259
LogD:	2.763
LogS:	-3.664
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.882
Synthetic Accessibility Score:	3.962
Fsp3:	0.65
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:	-4.681
MDCK Permeability:	1.7005144400172867e-05
Pgp-inhibitor:	0.163
Pgp-substrate:	0.575
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	89.4485855102539%
Volume Distribution (VD):	0.752
Pgp-substrate:	16.891220092773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.813
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.613
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.77

ADMET: Excretion

Clearance (CL):	9.739
Half-life (T1/2):	0.258

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.048
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.601

Download Data

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

Natural Product: NPC471189

Natural Product ID:	NPC471189
*Common Name:**	3Beta,16-Dihydroxy-8,11,13-Abietatrien-2-One
IUPAC Name:	(2R,4aS,10aR)-2-hydroxy-7-(1-hydroxypropan-2-yl)-1,1,4a-trimethyl-4,9,10,10a-tetrahydro-2H-phenanthren-3-one
Synonyms:
Standard InCHIKey:	SVUCVTQMJOSTKG-NBLUKIFKSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(11-21)13-5-7-15-14(9-13)6-8-17-19(2,3)18(23)16(22)10-20(15,17)4/h5,7,9,12,17-18,21,23H,6,8,10-11H2,1-4H3/t12?,17-,18-,20+/m0/s1
SMILES:	OCC(c1ccc2c(c1)CC[C@@H]1[C@]2(C)CC(=O)[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386524
PubChem CID:	71726404
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
NPO32493	euonymus lutchuensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23755851]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[564050]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[564050]
NPT168	Cell Line	P388	Mus musculus	IC50	<	5.0	ug.mL-1	PMID[564050]

☑ 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 NPC471189 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	200
0.1-0.2	983
0.2-0.3	2077
0.3-0.4	6663
0.4-0.5	12099
0.5-0.6	16831
0.6-0.7	3372
0.7-0.8	405
0.8-0.85	50
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC471186
0.9279	High Similarity	NPC476645
0.9074	High Similarity	NPC471188
0.8962	High Similarity	NPC142326
0.8962	High Similarity	NPC94751
0.8738	High Similarity	NPC324602
0.8696	High Similarity	NPC133389
0.8696	High Similarity	NPC234337
0.8696	High Similarity	NPC183339
0.8636	High Similarity	NPC265513
0.8547	High Similarity	NPC293831
0.8547	High Similarity	NPC369
0.8532	High Similarity	NPC472979
0.8532	High Similarity	NPC27252
0.8519	High Similarity	NPC243601
0.8491	Intermediate Similarity	NPC133809
0.8491	Intermediate Similarity	NPC136810
0.8491	Intermediate Similarity	NPC128248
0.8455	Intermediate Similarity	NPC149455
0.8455	Intermediate Similarity	NPC64642
0.8455	Intermediate Similarity	NPC472982
0.8435	Intermediate Similarity	NPC80605
0.8435	Intermediate Similarity	NPC323440
0.8435	Intermediate Similarity	NPC222968
0.843	Intermediate Similarity	NPC478165
0.843	Intermediate Similarity	NPC478162
0.8426	Intermediate Similarity	NPC56168
0.8364	Intermediate Similarity	NPC472980
0.8348	Intermediate Similarity	NPC212891
0.8333	Intermediate Similarity	NPC181334
0.8333	Intermediate Similarity	NPC215419
0.8319	Intermediate Similarity	NPC143768
0.8319	Intermediate Similarity	NPC470253
0.8318	Intermediate Similarity	NPC225079
0.8305	Intermediate Similarity	NPC472981
0.8304	Intermediate Similarity	NPC475002
0.8304	Intermediate Similarity	NPC95126
0.8252	Intermediate Similarity	NPC220596
0.825	Intermediate Similarity	NPC471187
0.8224	Intermediate Similarity	NPC221825
0.8205	Intermediate Similarity	NPC318173
0.8197	Intermediate Similarity	NPC253681
0.8174	Intermediate Similarity	NPC221275
0.8165	Intermediate Similarity	NPC19856
0.813	Intermediate Similarity	NPC262936
0.813	Intermediate Similarity	NPC30491
0.812	Intermediate Similarity	NPC45794
0.8115	Intermediate Similarity	NPC87985
0.8103	Intermediate Similarity	NPC9274
0.8099	Intermediate Similarity	NPC198014
0.8087	Intermediate Similarity	NPC471721
0.8058	Intermediate Similarity	NPC298115
0.8037	Intermediate Similarity	NPC226041
0.8036	Intermediate Similarity	NPC112903
0.8031	Intermediate Similarity	NPC78307
0.8018	Intermediate Similarity	NPC474307
0.8017	Intermediate Similarity	NPC93181
0.8017	Intermediate Similarity	NPC273336
0.8017	Intermediate Similarity	NPC11250
0.8017	Intermediate Similarity	NPC182333
0.8016	Intermediate Similarity	NPC476847
0.8	Intermediate Similarity	NPC32322
0.8	Intermediate Similarity	NPC259703
0.8	Intermediate Similarity	NPC49272
0.8	Intermediate Similarity	NPC93287
0.7969	Intermediate Similarity	NPC474659
0.7969	Intermediate Similarity	NPC23894
0.7951	Intermediate Similarity	NPC328107
0.7951	Intermediate Similarity	NPC77691
0.7946	Intermediate Similarity	NPC185763
0.7946	Intermediate Similarity	NPC83409
0.7946	Intermediate Similarity	NPC100767
0.7934	Intermediate Similarity	NPC253627
0.7931	Intermediate Similarity	NPC326664
0.7917	Intermediate Similarity	NPC472679
0.7917	Intermediate Similarity	NPC472680
0.7913	Intermediate Similarity	NPC186128
0.7913	Intermediate Similarity	NPC292834
0.7905	Intermediate Similarity	NPC125226
0.7881	Intermediate Similarity	NPC472862
0.7881	Intermediate Similarity	NPC92
0.7881	Intermediate Similarity	NPC469663
0.7881	Intermediate Similarity	NPC469843
0.7876	Intermediate Similarity	NPC21929
0.7869	Intermediate Similarity	NPC176208
0.7845	Intermediate Similarity	NPC469547
0.7838	Intermediate Similarity	NPC247976
0.7833	Intermediate Similarity	NPC202015
0.7823	Intermediate Similarity	NPC137750
0.7807	Intermediate Similarity	NPC475006
0.7805	Intermediate Similarity	NPC307139
0.7788	Intermediate Similarity	NPC193640
0.7788	Intermediate Similarity	NPC475905
0.7788	Intermediate Similarity	NPC25385
0.7787	Intermediate Similarity	NPC162935
0.7787	Intermediate Similarity	NPC249340
0.7787	Intermediate Similarity	NPC154696
0.7786	Intermediate Similarity	NPC475957
0.7778	Intermediate Similarity	NPC196673
0.7769	Intermediate Similarity	NPC318552
0.7769	Intermediate Similarity	NPC190501
0.776	Intermediate Similarity	NPC5486
0.776	Intermediate Similarity	NPC71610
0.7759	Intermediate Similarity	NPC280789
0.7736	Intermediate Similarity	NPC141607
0.7736	Intermediate Similarity	NPC187725
0.7734	Intermediate Similarity	NPC471851
0.7731	Intermediate Similarity	NPC38893
0.7731	Intermediate Similarity	NPC219112
0.7731	Intermediate Similarity	NPC105141
0.7731	Intermediate Similarity	NPC477137
0.7731	Intermediate Similarity	NPC308311
0.7731	Intermediate Similarity	NPC242764
0.7724	Intermediate Similarity	NPC121168
0.7712	Intermediate Similarity	NPC186933
0.7705	Intermediate Similarity	NPC241001
0.7699	Intermediate Similarity	NPC172483
0.7699	Intermediate Similarity	NPC134120
0.7686	Intermediate Similarity	NPC42657
0.768	Intermediate Similarity	NPC275576
0.7672	Intermediate Similarity	NPC133308
0.7667	Intermediate Similarity	NPC477136
0.7661	Intermediate Similarity	NPC472681
0.7661	Intermediate Similarity	NPC85511
0.7661	Intermediate Similarity	NPC318067
0.7658	Intermediate Similarity	NPC469481
0.7647	Intermediate Similarity	NPC147179
0.7647	Intermediate Similarity	NPC35797
0.7647	Intermediate Similarity	NPC192948
0.7642	Intermediate Similarity	NPC269923
0.7642	Intermediate Similarity	NPC167323
0.7634	Intermediate Similarity	NPC103082
0.7627	Intermediate Similarity	NPC67377
0.7619	Intermediate Similarity	NPC470753
0.7619	Intermediate Similarity	NPC473220
0.7619	Intermediate Similarity	NPC169913
0.7615	Intermediate Similarity	NPC310662
0.7615	Intermediate Similarity	NPC185208
0.7615	Intermediate Similarity	NPC219573
0.7611	Intermediate Similarity	NPC472222
0.7611	Intermediate Similarity	NPC472221
0.7603	Intermediate Similarity	NPC254233
0.7603	Intermediate Similarity	NPC471671
0.7594	Intermediate Similarity	NPC474250
0.7583	Intermediate Similarity	NPC308828
0.7578	Intermediate Similarity	NPC276238
0.7578	Intermediate Similarity	NPC171460
0.7574	Intermediate Similarity	NPC478164
0.7565	Intermediate Similarity	NPC211439
0.7563	Intermediate Similarity	NPC268160
0.7561	Intermediate Similarity	NPC476234
0.7559	Intermediate Similarity	NPC176130
0.7559	Intermediate Similarity	NPC84672
0.7559	Intermediate Similarity	NPC115797
0.7559	Intermediate Similarity	NPC51448
0.7559	Intermediate Similarity	NPC69424
0.7559	Intermediate Similarity	NPC78364
0.7557	Intermediate Similarity	NPC202225
0.7545	Intermediate Similarity	NPC239185
0.7545	Intermediate Similarity	NPC289201
0.7541	Intermediate Similarity	NPC469644
0.754	Intermediate Similarity	NPC470765
0.7538	Intermediate Similarity	NPC165612
0.7523	Intermediate Similarity	NPC172925
0.7523	Intermediate Similarity	NPC206764
0.7522	Intermediate Similarity	NPC274443
0.7522	Intermediate Similarity	NPC329556
0.7521	Intermediate Similarity	NPC172219
0.7521	Intermediate Similarity	NPC474057
0.7521	Intermediate Similarity	NPC304510
0.752	Intermediate Similarity	NPC12881
0.752	Intermediate Similarity	NPC140118
0.75	Intermediate Similarity	NPC62138
0.75	Intermediate Similarity	NPC264728
0.75	Intermediate Similarity	NPC476993
0.75	Intermediate Similarity	NPC248068
0.7481	Intermediate Similarity	NPC475346
0.7481	Intermediate Similarity	NPC477139
0.7481	Intermediate Similarity	NPC475457
0.7481	Intermediate Similarity	NPC203486
0.7481	Intermediate Similarity	NPC126516
0.7481	Intermediate Similarity	NPC475627
0.7481	Intermediate Similarity	NPC18982
0.748	Intermediate Similarity	NPC478121
0.748	Intermediate Similarity	NPC171007
0.748	Intermediate Similarity	NPC473136
0.748	Intermediate Similarity	NPC190849
0.748	Intermediate Similarity	NPC269598
0.7478	Intermediate Similarity	NPC85560
0.7478	Intermediate Similarity	NPC37914
0.7478	Intermediate Similarity	NPC244933
0.7477	Intermediate Similarity	NPC86670
0.7477	Intermediate Similarity	NPC70940
0.7477	Intermediate Similarity	NPC317280
0.7477	Intermediate Similarity	NPC329387
0.7477	Intermediate Similarity	NPC134882
0.7477	Intermediate Similarity	NPC274455
0.7464	Intermediate Similarity	NPC478160
0.7462	Intermediate Similarity	NPC291001
0.746	Intermediate Similarity	NPC75432

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 NPC471189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	820
0.2-0.3	1206
0.3-0.4	2917
0.4-0.5	2318
0.5-0.6	1344
0.6-0.7	308
0.7-0.8	40
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7982	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD2629	Approved
0.7769	Intermediate Similarity	NPD3019	Approved
0.7727	Intermediate Similarity	NPD2066	Phase 3
0.7712	Intermediate Similarity	NPD5951	Approved
0.7667	Intermediate Similarity	NPD7610	Discontinued
0.7664	Intermediate Similarity	NPD1088	Approved
0.7647	Intermediate Similarity	NPD3317	Approved
0.7623	Intermediate Similarity	NPD2932	Approved
0.7545	Intermediate Similarity	NPD3495	Discontinued
0.7542	Intermediate Similarity	NPD7094	Approved
0.7542	Intermediate Similarity	NPD6858	Approved
0.7523	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD1693	Approved
0.7522	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD1930	Approved
0.7522	Intermediate Similarity	NPD1929	Approved
0.7522	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1090	Approved
0.7477	Intermediate Similarity	NPD1089	Approved
0.7477	Intermediate Similarity	NPD1086	Approved
0.7419	Intermediate Similarity	NPD3023	Approved
0.7419	Intermediate Similarity	NPD3026	Approved
0.7398	Intermediate Similarity	NPD3024	Approved
0.7398	Intermediate Similarity	NPD3025	Approved
0.7383	Intermediate Similarity	NPD800	Approved
0.7355	Intermediate Similarity	NPD4198	Discontinued
0.7339	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6663	Approved
0.7328	Intermediate Similarity	NPD7961	Discontinued
0.7317	Intermediate Similarity	NPD3091	Approved
0.7308	Intermediate Similarity	NPD7008	Discontinued
0.7304	Intermediate Similarity	NPD1237	Approved
0.7297	Intermediate Similarity	NPD1989	Approved
0.7287	Intermediate Similarity	NPD5736	Approved
0.7273	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1239	Approved
0.7232	Intermediate Similarity	NPD1564	Approved
0.7232	Intermediate Similarity	NPD1565	Approved
0.7232	Intermediate Similarity	NPD1566	Phase 3
0.72	Intermediate Similarity	NPD3095	Discontinued
0.7196	Intermediate Similarity	NPD1087	Approved
0.7194	Intermediate Similarity	NPD7236	Approved
0.7177	Intermediate Similarity	NPD7009	Phase 2
0.7176	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4879	Approved
0.7087	Intermediate Similarity	NPD3092	Approved
0.7063	Intermediate Similarity	NPD7239	Suspended
0.7063	Intermediate Similarity	NPD4199	Phase 3
0.7049	Intermediate Similarity	NPD6010	Discontinued
0.7018	Intermediate Similarity	NPD9495	Approved
0.7008	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1651	Approved
0.6983	Remote Similarity	NPD1932	Approved
0.6964	Remote Similarity	NPD1563	Approved
0.694	Remote Similarity	NPD7714	Approved
0.694	Remote Similarity	NPD7715	Approved
0.6923	Remote Similarity	NPD1283	Approved
0.6917	Remote Similarity	NPD2329	Discontinued
0.6917	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5347	Phase 2
0.6909	Remote Similarity	NPD5346	Phase 2
0.6905	Remote Similarity	NPD7741	Discontinued
0.6897	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7631	Approved
0.687	Remote Similarity	NPD3094	Phase 2
0.6847	Remote Similarity	NPD3673	Approved
0.6847	Remote Similarity	NPD3672	Approved
0.6833	Remote Similarity	NPD2342	Discontinued
0.6829	Remote Similarity	NPD7635	Approved
0.6822	Remote Similarity	NPD5618	Discontinued
0.6822	Remote Similarity	NPD1201	Approved
0.6822	Remote Similarity	NPD9491	Approved
0.6812	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7798	Approved
0.6809	Remote Similarity	NPD7003	Approved
0.6792	Remote Similarity	NPD226	Approved
0.6786	Remote Similarity	NPD7609	Phase 3
0.678	Remote Similarity	NPD6647	Phase 2
0.678	Remote Similarity	NPD5765	Approved
0.6765	Remote Similarity	NPD4140	Approved
0.6754	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6049	Phase 2
0.675	Remote Similarity	NPD6685	Approved
0.6729	Remote Similarity	NPD3667	Approved
0.6727	Remote Similarity	NPD4793	Discontinued
0.6723	Remote Similarity	NPD5909	Discontinued
0.6695	Remote Similarity	NPD4719	Phase 2
0.6693	Remote Similarity	NPD6065	Approved
0.6692	Remote Similarity	NPD1281	Approved
0.6691	Remote Similarity	NPD8032	Phase 2
0.6691	Remote Similarity	NPD7305	Phase 1
0.669	Remote Similarity	NPD8166	Discontinued
0.669	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD7725	Approved
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD5125	Phase 3
0.6667	Remote Similarity	NPD5306	Approved
0.6667	Remote Similarity	NPD4059	Approved
0.6667	Remote Similarity	NPD5126	Approved
0.6642	Remote Similarity	NPD7084	Phase 3
0.6641	Remote Similarity	NPD4878	Approved
0.6639	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3618	Phase 1
0.6623	Remote Similarity	NPD7057	Phase 3
0.6623	Remote Similarity	NPD7058	Phase 2
0.6617	Remote Similarity	NPD1470	Approved
0.6606	Remote Similarity	NPD4786	Approved
0.6589	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4766	Approved
0.6585	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD650	Approved
0.6567	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6085	Phase 2
0.6565	Remote Similarity	NPD4806	Approved
0.6565	Remote Similarity	NPD4807	Approved
0.6552	Remote Similarity	NPD5221	Approved
0.6552	Remote Similarity	NPD5222	Approved
0.6552	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD2345	Approved
0.6532	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3642	Approved
0.6532	Remote Similarity	NPD3644	Approved
0.6532	Remote Similarity	NPD3643	Approved
0.6525	Remote Similarity	NPD5406	Approved
0.6525	Remote Similarity	NPD5408	Approved
0.6525	Remote Similarity	NPD5404	Approved
0.6525	Remote Similarity	NPD5405	Approved
0.6525	Remote Similarity	NPD3020	Approved
0.6522	Remote Similarity	NPD2979	Phase 3
0.6518	Remote Similarity	NPD1101	Approved
0.6512	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4479	Discontinued
0.6509	Remote Similarity	NPD225	Approved
0.6509	Remote Similarity	NPD227	Approved
0.6508	Remote Similarity	NPD2650	Approved
0.6508	Remote Similarity	NPD2652	Approved
0.6507	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5173	Approved
0.6496	Remote Similarity	NPD6798	Discontinued
0.6491	Remote Similarity	NPD6079	Approved
0.6491	Remote Similarity	NPD7515	Phase 2
0.6489	Remote Similarity	NPD4135	Approved
0.6489	Remote Similarity	NPD4106	Approved
0.6489	Remote Similarity	NPD4136	Approved
0.6486	Remote Similarity	NPD5279	Phase 3
0.6484	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4574	Approved
0.6484	Remote Similarity	NPD4576	Approved
0.6475	Remote Similarity	NPD5735	Approved
0.6475	Remote Similarity	NPD6355	Discontinued
0.6466	Remote Similarity	NPD5327	Phase 3
0.6466	Remote Similarity	NPD4814	Discontinued
0.6466	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5157	Phase 1
0.6466	Remote Similarity	NPD5159	Phase 2
0.646	Remote Similarity	NPD5328	Approved
0.6454	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1317	Discontinued
0.6452	Remote Similarity	NPD2067	Discontinued
0.6449	Remote Similarity	NPD9490	Approved
0.6444	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4624	Approved
0.6443	Remote Similarity	NPD7458	Discontinued
0.6443	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4216	Approved
0.6439	Remote Similarity	NPD3132	Approved
0.6439	Remote Similarity	NPD2610	Approved
0.6439	Remote Similarity	NPD2608	Approved
0.6439	Remote Similarity	NPD2611	Approved
0.6439	Remote Similarity	NPD3131	Approved
0.6439	Remote Similarity	NPD4218	Approved
0.6439	Remote Similarity	NPD4217	Approved
0.6439	Remote Similarity	NPD4215	Approved
0.6439	Remote Similarity	NPD2612	Approved
0.6439	Remote Similarity	NPD2609	Approved
0.6438	Remote Similarity	NPD8165	Discontinued
0.6429	Remote Similarity	NPD4097	Suspended
0.6412	Remote Similarity	NPD4626	Approved
0.641	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4697	Phase 3
0.641	Remote Similarity	NPD1809	Phase 2
0.6408	Remote Similarity	NPD2438	Suspended
0.6408	Remote Similarity	NPD6099	Approved
0.6408	Remote Similarity	NPD6100	Approved
0.6403	Remote Similarity	NPD3620	Phase 2
0.6403	Remote Similarity	NPD4060	Phase 1
0.6403	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD1018	Approved
0.6391	Remote Similarity	NPD3972	Approved
0.6391	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5285	Approved
0.6387	Remote Similarity	NPD5286	Approved
0.6387	Remote Similarity	NPD4696	Approved
0.6379	Remote Similarity	NPD3719	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