NPASS Compound

Structure

NPC189745 OpenBabel07101718182D 23 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 0.5000 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 -0.0000 1.0000 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 -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 -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 0.8660 0.5000 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 1 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 1 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 6 0 0 0 17 23 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	358.461
LogP:	2.88
LogD:	2.984
LogS:	-3.2
# Rotatable Bonds:	5
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	4.553
Fsp3:	0.8
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:	-4.592
MDCK Permeability:	9.311648682341911e-06
Pgp-inhibitor:	0.034
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.519
Plasma Protein Binding (PPB):	52.65789031982422%
Volume Distribution (VD):	0.992
Pgp-substrate:	52.63563537597656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.096
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.31
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.459
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	4.72
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.604
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.721
Carcinogencity:	0.896
Eye Corrosion:	0.013
Eye Irritation:	0.242
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC189745

Natural Product ID:	NPC189745
*Common Name:**	(12Z,14R)-Labda-8(17),12-Diene-14,15,16-Triol
IUPAC Name:	(2R,3Z)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]butane-1,2,4-triol
Synonyms:
Standard InCHIKey:	QJBFATPMWCHROY-XYNBGEFLSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-14-6-9-18-19(2,3)10-5-11-20(18,4)16(14)8-7-15(12-21)17(23)13-22/h7,16-18,21-23H,1,5-6,8-13H2,2-4H3/b15-7-/t16-,17-,18-,20+/m0/s1
SMILES:	OC[C@@H](/C(=CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C)/CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333384
PubChem CID:	71578896
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
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23394284]
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31457	Amomum kravanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	10.0	%	PMID[494335]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	90.0	%	PMID[494335]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[494335]

☑ 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 NPC189745 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	161
0.1-0.2	1389
0.2-0.3	6746
0.3-0.4	16071
0.4-0.5	8741
0.5-0.6	6864
0.6-0.7	2282
0.7-0.8	411
0.8-0.85	27
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8529	High Similarity	NPC250977
0.8514	High Similarity	NPC83351
0.8514	High Similarity	NPC167891
0.8406	Intermediate Similarity	NPC69649
0.8406	Intermediate Similarity	NPC68703
0.831	Intermediate Similarity	NPC34834
0.8243	Intermediate Similarity	NPC274079
0.8243	Intermediate Similarity	NPC477925
0.8219	Intermediate Similarity	NPC306727
0.8169	Intermediate Similarity	NPC473893
0.8154	Intermediate Similarity	NPC11130
0.8143	Intermediate Similarity	NPC114651
0.8133	Intermediate Similarity	NPC91594
0.8133	Intermediate Similarity	NPC477924
0.8108	Intermediate Similarity	NPC66566
0.8108	Intermediate Similarity	NPC477923
0.8101	Intermediate Similarity	NPC185568
0.8052	Intermediate Similarity	NPC96362
0.8026	Intermediate Similarity	NPC476314
0.7975	Intermediate Similarity	NPC474634
0.7975	Intermediate Similarity	NPC317458
0.7973	Intermediate Similarity	NPC471797
0.7973	Intermediate Similarity	NPC201048
0.7973	Intermediate Similarity	NPC476366
0.7949	Intermediate Similarity	NPC476646
0.7945	Intermediate Similarity	NPC242001
0.7927	Intermediate Similarity	NPC67872
0.7922	Intermediate Similarity	NPC47982
0.7922	Intermediate Similarity	NPC84694
0.7922	Intermediate Similarity	NPC143182
0.7922	Intermediate Similarity	NPC81306
0.7922	Intermediate Similarity	NPC109546
0.7922	Intermediate Similarity	NPC28862
0.7895	Intermediate Similarity	NPC470711
0.7895	Intermediate Similarity	NPC130136
0.7895	Intermediate Similarity	NPC470758
0.7875	Intermediate Similarity	NPC83702
0.7867	Intermediate Similarity	NPC313179
0.7867	Intermediate Similarity	NPC171148
0.7867	Intermediate Similarity	NPC291503
0.7867	Intermediate Similarity	NPC32832
0.7867	Intermediate Similarity	NPC69383
0.7848	Intermediate Similarity	NPC101462
0.7838	Intermediate Similarity	NPC68443
0.7838	Intermediate Similarity	NPC471799
0.7831	Intermediate Similarity	NPC470361
0.7821	Intermediate Similarity	NPC287749
0.7821	Intermediate Similarity	NPC234193
0.7808	Intermediate Similarity	NPC145498
0.7805	Intermediate Similarity	NPC470620
0.7794	Intermediate Similarity	NPC471081
0.7792	Intermediate Similarity	NPC474216
0.7778	Intermediate Similarity	NPC208999
0.7778	Intermediate Similarity	NPC471238
0.7763	Intermediate Similarity	NPC244488
0.7763	Intermediate Similarity	NPC315261
0.7763	Intermediate Similarity	NPC253190
0.7763	Intermediate Similarity	NPC470749
0.7763	Intermediate Similarity	NPC247325
0.7763	Intermediate Similarity	NPC265588
0.7761	Intermediate Similarity	NPC181872
0.775	Intermediate Similarity	NPC320548
0.775	Intermediate Similarity	NPC42476
0.7746	Intermediate Similarity	NPC202017
0.7746	Intermediate Similarity	NPC476406
0.7738	Intermediate Similarity	NPC3345
0.7738	Intermediate Similarity	NPC329596
0.7738	Intermediate Similarity	NPC204188
0.7738	Intermediate Similarity	NPC11216
0.7738	Intermediate Similarity	NPC80561
0.7738	Intermediate Similarity	NPC291484
0.7733	Intermediate Similarity	NPC91858
0.7733	Intermediate Similarity	NPC243342
0.7733	Intermediate Similarity	NPC477138
0.7722	Intermediate Similarity	NPC159148
0.7722	Intermediate Similarity	NPC209620
0.7722	Intermediate Similarity	NPC249423
0.7722	Intermediate Similarity	NPC264245
0.7722	Intermediate Similarity	NPC23852
0.7714	Intermediate Similarity	NPC290367
0.7711	Intermediate Similarity	NPC474668
0.7703	Intermediate Similarity	NPC167706
0.7703	Intermediate Similarity	NPC471271
0.7703	Intermediate Similarity	NPC471268
0.7703	Intermediate Similarity	NPC477792
0.7692	Intermediate Similarity	NPC233295
0.7692	Intermediate Similarity	NPC209430
0.7692	Intermediate Similarity	NPC30986
0.7692	Intermediate Similarity	NPC328714
0.7671	Intermediate Similarity	NPC167272
0.7671	Intermediate Similarity	NPC9942
0.7671	Intermediate Similarity	NPC269877
0.7671	Intermediate Similarity	NPC474248
0.7671	Intermediate Similarity	NPC471560
0.7654	Intermediate Similarity	NPC238992
0.7654	Intermediate Similarity	NPC205845
0.7647	Intermediate Similarity	NPC97404
0.7647	Intermediate Similarity	NPC41554
0.7647	Intermediate Similarity	NPC122239
0.7647	Intermediate Similarity	NPC475931
0.7632	Intermediate Similarity	NPC319090
0.7632	Intermediate Similarity	NPC133580
0.7632	Intermediate Similarity	NPC328104
0.7625	Intermediate Similarity	NPC155521
0.7625	Intermediate Similarity	NPC49964
0.7625	Intermediate Similarity	NPC189972
0.7625	Intermediate Similarity	NPC50964
0.7619	Intermediate Similarity	NPC259875
0.7619	Intermediate Similarity	NPC187785
0.76	Intermediate Similarity	NPC474743
0.76	Intermediate Similarity	NPC265485
0.76	Intermediate Similarity	NPC220939
0.76	Intermediate Similarity	NPC474140
0.7595	Intermediate Similarity	NPC241290
0.7595	Intermediate Similarity	NPC295131
0.7595	Intermediate Similarity	NPC281880
0.7595	Intermediate Similarity	NPC209944
0.7595	Intermediate Similarity	NPC324772
0.7595	Intermediate Similarity	NPC474592
0.7595	Intermediate Similarity	NPC164840
0.7568	Intermediate Similarity	NPC9161
0.7568	Intermediate Similarity	NPC92801
0.7568	Intermediate Similarity	NPC49422
0.7564	Intermediate Similarity	NPC11908
0.7564	Intermediate Similarity	NPC473943
0.7561	Intermediate Similarity	NPC266511
0.7534	Intermediate Similarity	NPC96484
0.7534	Intermediate Similarity	NPC276616
0.7532	Intermediate Similarity	NPC321016
0.7532	Intermediate Similarity	NPC107059
0.7532	Intermediate Similarity	NPC321381
0.7531	Intermediate Similarity	NPC475789
0.7531	Intermediate Similarity	NPC253402
0.7531	Intermediate Similarity	NPC159168
0.7531	Intermediate Similarity	NPC470384
0.75	Intermediate Similarity	NPC47761
0.75	Intermediate Similarity	NPC326310
0.75	Intermediate Similarity	NPC476039
0.75	Intermediate Similarity	NPC311736
0.75	Intermediate Similarity	NPC133588
0.75	Intermediate Similarity	NPC474752
0.75	Intermediate Similarity	NPC474731
0.75	Intermediate Similarity	NPC267027
0.75	Intermediate Similarity	NPC474531
0.75	Intermediate Similarity	NPC27395
0.75	Intermediate Similarity	NPC7505
0.75	Intermediate Similarity	NPC82986
0.75	Intermediate Similarity	NPC474759
0.75	Intermediate Similarity	NPC469534
0.75	Intermediate Similarity	NPC320525
0.75	Intermediate Similarity	NPC471270
0.75	Intermediate Similarity	NPC222366
0.75	Intermediate Similarity	NPC149680
0.75	Intermediate Similarity	NPC469593
0.75	Intermediate Similarity	NPC104644
0.75	Intermediate Similarity	NPC226848
0.75	Intermediate Similarity	NPC329090
0.75	Intermediate Similarity	NPC286669
0.75	Intermediate Similarity	NPC474683
0.75	Intermediate Similarity	NPC469533
0.747	Intermediate Similarity	NPC152808
0.747	Intermediate Similarity	NPC6391
0.747	Intermediate Similarity	NPC293287
0.747	Intermediate Similarity	NPC237344
0.747	Intermediate Similarity	NPC175145
0.747	Intermediate Similarity	NPC470955
0.747	Intermediate Similarity	NPC475069
0.7468	Intermediate Similarity	NPC53744
0.7467	Intermediate Similarity	NPC471272
0.7467	Intermediate Similarity	NPC23954
0.7465	Intermediate Similarity	NPC225415
0.7465	Intermediate Similarity	NPC96793
0.7465	Intermediate Similarity	NPC323424
0.7439	Intermediate Similarity	NPC473157
0.7439	Intermediate Similarity	NPC102048
0.7436	Intermediate Similarity	NPC155986
0.7436	Intermediate Similarity	NPC198968
0.7436	Intermediate Similarity	NPC318495
0.7436	Intermediate Similarity	NPC471798
0.7436	Intermediate Similarity	NPC325946
0.7429	Intermediate Similarity	NPC475251
0.7412	Intermediate Similarity	NPC115607
0.7412	Intermediate Similarity	NPC477606
0.7412	Intermediate Similarity	NPC79027
0.7407	Intermediate Similarity	NPC30166
0.7407	Intermediate Similarity	NPC212083
0.7407	Intermediate Similarity	NPC471408
0.7407	Intermediate Similarity	NPC47763
0.7407	Intermediate Similarity	NPC296701
0.7407	Intermediate Similarity	NPC218616
0.7403	Intermediate Similarity	NPC28657
0.7403	Intermediate Similarity	NPC285893
0.7403	Intermediate Similarity	NPC22105
0.7403	Intermediate Similarity	NPC134847
0.7403	Intermediate Similarity	NPC136188
0.7403	Intermediate Similarity	NPC230301
0.7403	Intermediate Similarity	NPC304309
0.7403	Intermediate Similarity	NPC288035
0.7403	Intermediate Similarity	NPC162742
0.7397	Intermediate Similarity	NPC163290

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 NPC189745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1736
0.2-0.3	4324
0.3-0.4	2152
0.4-0.5	470
0.5-0.6	252
0.6-0.7	39
0.7-0.8	29
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD6925	Approved
0.7895	Intermediate Similarity	NPD5776	Phase 2
0.7867	Intermediate Similarity	NPD8264	Approved
0.7821	Intermediate Similarity	NPD7332	Phase 2
0.7821	Intermediate Similarity	NPD7514	Phase 3
0.7792	Intermediate Similarity	NPD7145	Approved
0.7792	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6933	Approved
0.7722	Intermediate Similarity	NPD6902	Approved
0.7692	Intermediate Similarity	NPD6929	Approved
0.7671	Intermediate Similarity	NPD6922	Approved
0.7671	Intermediate Similarity	NPD6923	Approved
0.7595	Intermediate Similarity	NPD6931	Approved
0.7595	Intermediate Similarity	NPD6930	Phase 2
0.7568	Intermediate Similarity	NPD7143	Approved
0.7568	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.75	Intermediate Similarity	NPD6898	Phase 1
0.7467	Intermediate Similarity	NPD7151	Approved
0.7467	Intermediate Similarity	NPD7150	Approved
0.7467	Intermediate Similarity	NPD7152	Approved
0.7439	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6932	Approved
0.7403	Intermediate Similarity	NPD6942	Approved
0.7403	Intermediate Similarity	NPD7339	Approved
0.7381	Intermediate Similarity	NPD7524	Approved
0.7317	Intermediate Similarity	NPD6695	Phase 3
0.7308	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7645	Phase 2
0.725	Intermediate Similarity	NPD6683	Phase 2
0.7183	Intermediate Similarity	NPD368	Approved
0.716	Intermediate Similarity	NPD7525	Registered
0.716	Intermediate Similarity	NPD7509	Discontinued
0.7143	Intermediate Similarity	NPD6893	Approved
0.6977	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7750	Discontinued
0.6957	Remote Similarity	NPD4219	Approved
0.6854	Remote Similarity	NPD7637	Suspended
0.6824	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD3667	Approved
0.6774	Remote Similarity	NPD4225	Approved
0.6742	Remote Similarity	NPD7136	Phase 2
0.6709	Remote Similarity	NPD4732	Discontinued
0.6667	Remote Similarity	NPD7087	Discontinued
0.6628	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4784	Approved
0.6625	Remote Similarity	NPD4785	Approved
0.6582	Remote Similarity	NPD4243	Approved
0.6437	Remote Similarity	NPD3666	Approved
0.6437	Remote Similarity	NPD3133	Approved
0.6437	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD6640	Phase 3
0.6353	Remote Similarity	NPD4820	Approved
0.6353	Remote Similarity	NPD4819	Approved
0.6353	Remote Similarity	NPD4821	Approved
0.6353	Remote Similarity	NPD4822	Approved
0.6338	Remote Similarity	NPD342	Phase 1
0.631	Remote Similarity	NPD4271	Approved
0.631	Remote Similarity	NPD4268	Approved
0.631	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3618	Phase 1
0.6264	Remote Similarity	NPD5328	Approved
0.6238	Remote Similarity	NPD6686	Approved
0.6237	Remote Similarity	NPD6399	Phase 3
0.6212	Remote Similarity	NPD4265	Approved
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.6163	Remote Similarity	NPD4695	Discontinued
0.6163	Remote Similarity	NPD4748	Discontinued
0.6163	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4190	Phase 3
0.6145	Remote Similarity	NPD5275	Approved
0.6129	Remote Similarity	NPD6079	Approved
0.6129	Remote Similarity	NPD7515	Phase 2
0.6122	Remote Similarity	NPD5344	Discontinued
0.6111	Remote Similarity	NPD4623	Approved
0.6111	Remote Similarity	NPD5279	Phase 3
0.6111	Remote Similarity	NPD4519	Discontinued
0.6087	Remote Similarity	NPD4753	Phase 2
0.6082	Remote Similarity	NPD7638	Approved
0.6067	Remote Similarity	NPD3668	Phase 3
0.6064	Remote Similarity	NPD4202	Approved
0.6064	Remote Similarity	NPD5778	Approved
0.6064	Remote Similarity	NPD5779	Approved
0.6061	Remote Similarity	NPD5211	Phase 2
0.6053	Remote Similarity	NPD4194	Approved
0.6053	Remote Similarity	NPD4192	Approved
0.6053	Remote Similarity	NPD4193	Approved
0.6053	Remote Similarity	NPD4191	Approved
0.6047	Remote Similarity	NPD4195	Approved
0.6022	Remote Similarity	NPD46	Approved
0.6022	Remote Similarity	NPD6698	Approved
0.598	Remote Similarity	NPD6412	Phase 2
0.5979	Remote Similarity	NPD4755	Approved
0.596	Remote Similarity	NPD4159	Approved
0.5957	Remote Similarity	NPD7983	Approved
0.5957	Remote Similarity	NPD6411	Approved
0.5955	Remote Similarity	NPD5331	Approved
0.5955	Remote Similarity	NPD5362	Discontinued
0.5955	Remote Similarity	NPD7154	Phase 3
0.5955	Remote Similarity	NPD5332	Approved
0.5941	Remote Similarity	NPD5141	Approved
0.5926	Remote Similarity	NPD7115	Discovery
0.5926	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4137	Phase 3
0.5914	Remote Similarity	NPD6051	Approved
0.5909	Remote Similarity	NPD4790	Discontinued
0.5897	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7333	Discontinued
0.5859	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD5286	Approved
0.5859	Remote Similarity	NPD4696	Approved
0.5859	Remote Similarity	NPD4700	Approved
0.5854	Remote Similarity	NPD4691	Approved
0.5854	Remote Similarity	NPD4747	Approved
0.5851	Remote Similarity	NPD7838	Discovery
0.5843	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4223	Phase 3
0.5843	Remote Similarity	NPD4270	Approved
0.5843	Remote Similarity	NPD4269	Approved
0.5843	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD7748	Approved
0.5824	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD5329	Approved
0.5824	Remote Similarity	NPD1696	Phase 3
0.5816	Remote Similarity	NPD6084	Phase 2
0.5816	Remote Similarity	NPD6083	Phase 2
0.5816	Remote Similarity	NPD7902	Approved
0.5802	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4252	Approved
0.5778	Remote Similarity	NPD6110	Phase 1
0.5778	Remote Similarity	NPD4788	Approved
0.5773	Remote Similarity	NPD5210	Approved
0.5773	Remote Similarity	NPD4629	Approved
0.5769	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD7521	Approved
0.5761	Remote Similarity	NPD7146	Approved
0.5761	Remote Similarity	NPD7334	Approved
0.5761	Remote Similarity	NPD6684	Approved
0.5761	Remote Similarity	NPD6409	Approved
0.5761	Remote Similarity	NPD5330	Approved
0.5745	Remote Similarity	NPD6101	Approved
0.5745	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4633	Approved
0.5743	Remote Similarity	NPD5224	Approved
0.5743	Remote Similarity	NPD5226	Approved
0.5743	Remote Similarity	NPD5225	Approved
0.5728	Remote Similarity	NPD6675	Approved
0.5728	Remote Similarity	NPD5739	Approved
0.5728	Remote Similarity	NPD7128	Approved
0.5728	Remote Similarity	NPD6402	Approved
0.5727	Remote Similarity	NPD7328	Approved
0.5727	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5221	Approved
0.5714	Remote Similarity	NPD4197	Approved
0.5714	Remote Similarity	NPD8033	Approved
0.57	Remote Similarity	NPD6648	Approved
0.5699	Remote Similarity	NPD4250	Approved
0.5699	Remote Similarity	NPD4251	Approved
0.5686	Remote Similarity	NPD5174	Approved
0.5686	Remote Similarity	NPD5175	Approved
0.5684	Remote Similarity	NPD5785	Approved
0.5676	Remote Similarity	NPD7516	Approved
0.566	Remote Similarity	NPD4634	Approved
0.5658	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5173	Approved
0.5652	Remote Similarity	NPD5363	Approved
0.5652	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4058	Approved
0.5647	Remote Similarity	NPD5733	Approved
0.5644	Remote Similarity	NPD5223	Approved
0.5638	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6903	Approved
0.5625	Remote Similarity	NPD8377	Approved
0.5625	Remote Similarity	NPD8294	Approved
0.5619	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD6899	Approved
0.5619	Remote Similarity	NPD6881	Approved
0.5618	Remote Similarity	NPD5368	Approved
0.56	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5290	Discontinued

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