NPASS Compound

Structure

NPC312480 OpenBabel07101718242D 23 24 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 -1.7321 -5.0000 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 -2.5000 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 -3.4641 -5.0000 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 0.0000 -2.0000 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 -4.5000 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 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 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 0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 14 16 1 0 0 0 0 15 21 1 6 0 0 0 16 19 1 1 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	2.8
LogD:	2.005
LogS:	-3.923
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	4.652
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.114
MDCK Permeability:	3.187480615451932e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.229
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	72.60337829589844%
Volume Distribution (VD):	0.452
Pgp-substrate:	22.148988723754883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	0.844
Half-life (T1/2):	0.744

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.149
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.723
Carcinogencity:	0.418
Eye Corrosion:	0.712
Eye Irritation:	0.911
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC312480

Natural Product ID:	NPC312480
*Common Name:**	2-Alpha-Hydroxylabda-8(17),12E,14-Trien-18-Oic Acid
IUPAC Name:	(1R,3R,4aR,5S,8aR)-3-hydroxy-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	USNLWGSHMJHWQY-FBIYPSPZSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-6-13(2)7-9-16-14(3)8-10-17-19(16,4)11-15(21)12-20(17,5)18(22)23/h6-7,15-17,21H,1,3,8-12H2,2,4-5H3,(H,22,23)/b13-7+/t15-,16+,17-,19-,20-/m1/s1
SMILES:	C=C/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@]1(C)C[C@@H](O)C[C@@]2(C)C(=O)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL434755
PubChem CID:	16109843
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
NPO23470	Orthosiphon labiatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17256988]
NPO32827	salvia africana-lutea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17256988]
NPO23470	Orthosiphon labiatus	Species	Lamiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	157000.0	nM	PMID[522904]

☑ 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 NPC312480 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	169
0.1-0.2	891
0.2-0.3	4092
0.3-0.4	11933
0.4-0.5	11361
0.5-0.6	7045
0.6-0.7	5258
0.7-0.8	1768
0.8-0.85	158
0.85-0.9	19
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8831	High Similarity	NPC237591
0.8831	High Similarity	NPC3753
0.881	High Similarity	NPC477926
0.8765	High Similarity	NPC473420
0.8718	High Similarity	NPC476844
0.8675	High Similarity	NPC139566
0.8659	High Similarity	NPC73882
0.8625	High Similarity	NPC269543
0.8625	High Similarity	NPC247783
0.8621	High Similarity	NPC301244
0.8605	High Similarity	NPC161751
0.8605	High Similarity	NPC474972
0.8605	High Similarity	NPC95246
0.8519	High Similarity	NPC474113
0.8506	High Similarity	NPC210037
0.8506	High Similarity	NPC290614
0.8506	High Similarity	NPC18872
0.8506	High Similarity	NPC7260
0.8506	High Similarity	NPC227467
0.8506	High Similarity	NPC120968
0.8506	High Similarity	NPC273621
0.8506	High Similarity	NPC477872
0.85	High Similarity	NPC474433
0.8471	Intermediate Similarity	NPC82979
0.8471	Intermediate Similarity	NPC325594
0.8471	Intermediate Similarity	NPC473226
0.8471	Intermediate Similarity	NPC73038
0.8471	Intermediate Similarity	NPC6979
0.8462	Intermediate Similarity	NPC68443
0.8427	Intermediate Similarity	NPC80365
0.8427	Intermediate Similarity	NPC49670
0.8409	Intermediate Similarity	NPC105189
0.8409	Intermediate Similarity	NPC187722
0.8395	Intermediate Similarity	NPC239098
0.8391	Intermediate Similarity	NPC84271
0.8391	Intermediate Similarity	NPC474686
0.8391	Intermediate Similarity	NPC102414
0.8391	Intermediate Similarity	NPC64872
0.8391	Intermediate Similarity	NPC25906
0.8391	Intermediate Similarity	NPC128496
0.8391	Intermediate Similarity	NPC77168
0.8391	Intermediate Similarity	NPC290972
0.8372	Intermediate Similarity	NPC142361
0.8372	Intermediate Similarity	NPC51700
0.8372	Intermediate Similarity	NPC102683
0.8372	Intermediate Similarity	NPC242468
0.8372	Intermediate Similarity	NPC68160
0.8372	Intermediate Similarity	NPC307426
0.8372	Intermediate Similarity	NPC142415
0.8372	Intermediate Similarity	NPC171203
0.8372	Intermediate Similarity	NPC18064
0.8372	Intermediate Similarity	NPC141292
0.8372	Intermediate Similarity	NPC98442
0.8372	Intermediate Similarity	NPC130577
0.8372	Intermediate Similarity	NPC293564
0.8372	Intermediate Similarity	NPC474684
0.8372	Intermediate Similarity	NPC88716
0.8354	Intermediate Similarity	NPC183503
0.8354	Intermediate Similarity	NPC103958
0.8354	Intermediate Similarity	NPC283908
0.8354	Intermediate Similarity	NPC161923
0.8353	Intermediate Similarity	NPC476602
0.8333	Intermediate Similarity	NPC45324
0.8333	Intermediate Similarity	NPC139459
0.8333	Intermediate Similarity	NPC474789
0.8333	Intermediate Similarity	NPC222845
0.8333	Intermediate Similarity	NPC162001
0.8333	Intermediate Similarity	NPC52108
0.8333	Intermediate Similarity	NPC470948
0.8333	Intermediate Similarity	NPC88310
0.8315	Intermediate Similarity	NPC470375
0.8315	Intermediate Similarity	NPC158059
0.8315	Intermediate Similarity	NPC202728
0.8315	Intermediate Similarity	NPC470376
0.8315	Intermediate Similarity	NPC229281
0.8315	Intermediate Similarity	NPC118519
0.8313	Intermediate Similarity	NPC14151
0.8295	Intermediate Similarity	NPC193750
0.8295	Intermediate Similarity	NPC46281
0.8295	Intermediate Similarity	NPC291028
0.8295	Intermediate Similarity	NPC232202
0.8295	Intermediate Similarity	NPC130278
0.8276	Intermediate Similarity	NPC290690
0.8276	Intermediate Similarity	NPC310752
0.8276	Intermediate Similarity	NPC182797
0.8276	Intermediate Similarity	NPC104560
0.8276	Intermediate Similarity	NPC40552
0.8276	Intermediate Similarity	NPC52169
0.8276	Intermediate Similarity	NPC181225
0.8276	Intermediate Similarity	NPC473242
0.8276	Intermediate Similarity	NPC473229
0.8276	Intermediate Similarity	NPC246708
0.8276	Intermediate Similarity	NPC292491
0.8276	Intermediate Similarity	NPC474512
0.8276	Intermediate Similarity	NPC17733
0.8276	Intermediate Similarity	NPC470629
0.8256	Intermediate Similarity	NPC72638
0.8256	Intermediate Similarity	NPC155011
0.825	Intermediate Similarity	NPC192540
0.825	Intermediate Similarity	NPC279666
0.8242	Intermediate Similarity	NPC471153
0.8242	Intermediate Similarity	NPC250757
0.8242	Intermediate Similarity	NPC301534
0.8222	Intermediate Similarity	NPC6818
0.8222	Intermediate Similarity	NPC191412
0.8222	Intermediate Similarity	NPC60692
0.8222	Intermediate Similarity	NPC114159
0.8214	Intermediate Similarity	NPC48362
0.8205	Intermediate Similarity	NPC91369
0.8202	Intermediate Similarity	NPC86266
0.8202	Intermediate Similarity	NPC110657
0.8202	Intermediate Similarity	NPC212301
0.8202	Intermediate Similarity	NPC38754
0.8182	Intermediate Similarity	NPC263393
0.8182	Intermediate Similarity	NPC143232
0.8182	Intermediate Similarity	NPC274330
0.8182	Intermediate Similarity	NPC470588
0.8182	Intermediate Similarity	NPC130520
0.8182	Intermediate Similarity	NPC293048
0.8182	Intermediate Similarity	NPC61543
0.8182	Intermediate Similarity	NPC474704
0.8182	Intermediate Similarity	NPC234346
0.8182	Intermediate Similarity	NPC225585
0.8182	Intermediate Similarity	NPC198664
0.8182	Intermediate Similarity	NPC127689
0.8182	Intermediate Similarity	NPC59263
0.8182	Intermediate Similarity	NPC270768
0.8182	Intermediate Similarity	NPC475921
0.8182	Intermediate Similarity	NPC121798
0.8171	Intermediate Similarity	NPC59436
0.8161	Intermediate Similarity	NPC233836
0.8161	Intermediate Similarity	NPC187376
0.8161	Intermediate Similarity	NPC71507
0.8161	Intermediate Similarity	NPC159046
0.8152	Intermediate Similarity	NPC21728
0.8148	Intermediate Similarity	NPC309399
0.8148	Intermediate Similarity	NPC69143
0.814	Intermediate Similarity	NPC52628
0.814	Intermediate Similarity	NPC329738
0.8132	Intermediate Similarity	NPC83693
0.8132	Intermediate Similarity	NPC53565
0.8132	Intermediate Similarity	NPC96916
0.8132	Intermediate Similarity	NPC290481
0.8125	Intermediate Similarity	NPC241854
0.8125	Intermediate Similarity	NPC301065
0.8125	Intermediate Similarity	NPC476046
0.8125	Intermediate Similarity	NPC251970
0.8118	Intermediate Similarity	NPC105173
0.8111	Intermediate Similarity	NPC63118
0.8111	Intermediate Similarity	NPC118490
0.8111	Intermediate Similarity	NPC107674
0.8111	Intermediate Similarity	NPC170220
0.8111	Intermediate Similarity	NPC470224
0.8111	Intermediate Similarity	NPC49776
0.8111	Intermediate Similarity	NPC474436
0.8111	Intermediate Similarity	NPC152897
0.8111	Intermediate Similarity	NPC141497
0.8111	Intermediate Similarity	NPC66429
0.8095	Intermediate Similarity	NPC209318
0.8095	Intermediate Similarity	NPC90055
0.8095	Intermediate Similarity	NPC121984
0.8095	Intermediate Similarity	NPC142244
0.8095	Intermediate Similarity	NPC223330
0.8095	Intermediate Similarity	NPC142163
0.8095	Intermediate Similarity	NPC474955
0.809	Intermediate Similarity	NPC86372
0.809	Intermediate Similarity	NPC470589
0.809	Intermediate Similarity	NPC46441
0.809	Intermediate Similarity	NPC126369
0.809	Intermediate Similarity	NPC172361
0.809	Intermediate Similarity	NPC111110
0.8072	Intermediate Similarity	NPC100906
0.8068	Intermediate Similarity	NPC247406
0.8068	Intermediate Similarity	NPC48866
0.8065	Intermediate Similarity	NPC186810
0.8065	Intermediate Similarity	NPC48647
0.8065	Intermediate Similarity	NPC57079
0.8065	Intermediate Similarity	NPC477813
0.8065	Intermediate Similarity	NPC108368
0.8049	Intermediate Similarity	NPC165711
0.8046	Intermediate Similarity	NPC55309
0.8046	Intermediate Similarity	NPC28252
0.8046	Intermediate Similarity	NPC475862
0.8046	Intermediate Similarity	NPC74363
0.8046	Intermediate Similarity	NPC329692
0.8046	Intermediate Similarity	NPC94666
0.8043	Intermediate Similarity	NPC157113
0.8043	Intermediate Similarity	NPC327179
0.8043	Intermediate Similarity	NPC204961
0.8043	Intermediate Similarity	NPC259733
0.8043	Intermediate Similarity	NPC88847
0.8043	Intermediate Similarity	NPC173744
0.8043	Intermediate Similarity	NPC158371
0.8043	Intermediate Similarity	NPC207922
0.8043	Intermediate Similarity	NPC62516
0.8043	Intermediate Similarity	NPC73004
0.8043	Intermediate Similarity	NPC9487
0.8043	Intermediate Similarity	NPC132824
0.8043	Intermediate Similarity	NPC116457
0.8023	Intermediate Similarity	NPC165064

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 NPC312480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1203
0.2-0.3	3525
0.3-0.4	2755
0.4-0.5	928
0.5-0.6	284
0.6-0.7	215
0.7-0.8	81
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
0.8046	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD3667	Approved
0.7912	Intermediate Similarity	NPD6399	Phase 3
0.7816	Intermediate Similarity	NPD4786	Approved
0.7802	Intermediate Similarity	NPD6411	Approved
0.7766	Intermediate Similarity	NPD7902	Approved
0.7727	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5279	Phase 3
0.7634	Intermediate Similarity	NPD7748	Approved
0.7614	Intermediate Similarity	NPD3665	Phase 1
0.7614	Intermediate Similarity	NPD3133	Approved
0.7614	Intermediate Similarity	NPD3666	Approved
0.7609	Intermediate Similarity	NPD6079	Approved
0.7609	Intermediate Similarity	NPD5281	Approved
0.7609	Intermediate Similarity	NPD5284	Approved
0.7582	Intermediate Similarity	NPD6101	Approved
0.7582	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5328	Approved
0.7527	Intermediate Similarity	NPD4202	Approved
0.7447	Intermediate Similarity	NPD7900	Approved
0.7447	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8035	Phase 2
0.7419	Intermediate Similarity	NPD8034	Phase 2
0.734	Intermediate Similarity	NPD5779	Approved
0.734	Intermediate Similarity	NPD5778	Approved
0.7327	Intermediate Similarity	NPD5697	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7262	Intermediate Similarity	NPD6926	Approved
0.7262	Intermediate Similarity	NPD6924	Approved
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7255	Intermediate Similarity	NPD6011	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7245	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD5286	Approved
0.7245	Intermediate Similarity	NPD4696	Approved
0.7229	Intermediate Similarity	NPD7152	Approved
0.7229	Intermediate Similarity	NPD7150	Approved
0.7229	Intermediate Similarity	NPD7151	Approved
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD4755	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7212	Intermediate Similarity	NPD6650	Approved
0.7212	Intermediate Similarity	NPD6649	Approved
0.7204	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD6372	Approved
0.7184	Intermediate Similarity	NPD6373	Approved
0.7184	Intermediate Similarity	NPD6014	Approved
0.7184	Intermediate Similarity	NPD6012	Approved
0.7176	Intermediate Similarity	NPD8264	Approved
0.7174	Intermediate Similarity	NPD3573	Approved
0.7172	Intermediate Similarity	NPD5223	Approved
0.7159	Intermediate Similarity	NPD4695	Discontinued
0.7159	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7525	Registered
0.7159	Intermediate Similarity	NPD7509	Discontinued
0.7157	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7126	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7108	Intermediate Similarity	NPD7143	Approved
0.7108	Intermediate Similarity	NPD7144	Approved
0.71	Intermediate Similarity	NPD5225	Approved
0.71	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD4633	Approved
0.71	Intermediate Similarity	NPD5226	Approved
0.71	Intermediate Similarity	NPD5224	Approved
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7093	Intermediate Similarity	NPD6933	Approved
0.7093	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7320	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD4700	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.7045	Intermediate Similarity	NPD7645	Phase 2
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD5174	Approved
0.703	Intermediate Similarity	NPD5175	Approved
0.7021	Intermediate Similarity	NPD4753	Phase 2
0.7011	Intermediate Similarity	NPD6116	Phase 1
0.701	Intermediate Similarity	NPD5210	Approved
0.701	Intermediate Similarity	NPD4629	Approved
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.6988	Remote Similarity	NPD6922	Approved
0.6988	Remote Similarity	NPD6923	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD7339	Approved
0.6977	Remote Similarity	NPD6942	Approved
0.6977	Remote Similarity	NPD8039	Approved
0.697	Remote Similarity	NPD5696	Approved
0.6966	Remote Similarity	NPD5368	Approved
0.6961	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6947	Remote Similarity	NPD5207	Approved
0.6916	Remote Similarity	NPD4632	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD6117	Approved
0.6889	Remote Similarity	NPD5369	Approved
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4694	Approved
0.6882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5280	Approved
0.6882	Remote Similarity	NPD4623	Approved
0.6882	Remote Similarity	NPD4519	Discontinued
0.6863	Remote Similarity	NPD4754	Approved
0.6854	Remote Similarity	NPD6929	Approved
0.6848	Remote Similarity	NPD4197	Approved
0.6837	Remote Similarity	NPD5695	Phase 3
0.6818	Remote Similarity	NPD6932	Approved
0.6813	Remote Similarity	NPD4270	Approved
0.6813	Remote Similarity	NPD6435	Approved
0.6813	Remote Similarity	NPD4269	Approved
0.6786	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD6930	Phase 2
0.6774	Remote Similarity	NPD5329	Approved
0.6762	Remote Similarity	NPD4730	Approved
0.6762	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD6686	Approved
0.6742	Remote Similarity	NPD6115	Approved
0.6742	Remote Similarity	NPD6697	Approved
0.6742	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6118	Approved
0.6742	Remote Similarity	NPD3617	Approved
0.6742	Remote Similarity	NPD6114	Approved
0.6742	Remote Similarity	NPD7145	Approved
0.6739	Remote Similarity	NPD5362	Discontinued
0.6739	Remote Similarity	NPD4788	Approved
0.6731	Remote Similarity	NPD4768	Approved
0.6731	Remote Similarity	NPD4767	Approved
0.6731	Remote Similarity	NPD6008	Approved
0.6727	Remote Similarity	NPD6009	Approved
0.6727	Remote Similarity	NPD6317	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6702	Remote Similarity	NPD6098	Approved
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.6701	Remote Similarity	NPD5694	Approved
0.6698	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4058	Approved
0.6637	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5250	Approved
0.6636	Remote Similarity	NPD5247	Approved
0.6636	Remote Similarity	NPD5248	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD6868	Approved
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD6274	Approved
0.6636	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5776	Phase 2
0.6629	Remote Similarity	NPD6925	Approved
0.6628	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7101	Approved
0.6607	Remote Similarity	NPD7100	Approved
0.6604	Remote Similarity	NPD5345	Clinical (unspecified phase)

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