NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.22
Volume:	282.94
LogP:	6.066
LogD:	3.414
LogS:	-4.786
# Rotatable Bonds:	12
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	1.755
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	2.323546323168557e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.519
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	98.47924041748047%
Volume Distribution (VD):	0.405
Pgp-substrate:	1.2266281843185425%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.354
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	2.458
Half-life (T1/2):	0.682

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.772
Carcinogencity:	0.07
Eye Corrosion:	0.974
Eye Irritation:	0.98
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC55023

Natural Product ID:	NPC55023
*Common Name:**	13-Methyltetradecanoic Acid
IUPAC Name:	13-methyltetradecanoic acid
Synonyms:	13-Methyl Tetradecanoic Acid
Standard InCHIKey:	ZOCYQVNGROEVLU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H30O2/c1-14(2)12-10-8-6-4-3-5-7-9-11-13-15(16)17/h14H,3-13H2,1-2H3,(H,16,17)
SMILES:	CC(CCCCCCCCCCCC(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495851
PubChem CID:	151014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843583]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791477]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24927	Calyx podatypa	Species	Phloeodictyidae	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
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	3.13	ug.mL-1	PMID[544648]

☑ 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 NPC55023 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	504
0.1-0.2	8009
0.2-0.3	18579
0.3-0.4	9753
0.4-0.5	4775
0.5-0.6	831
0.6-0.7	162
0.7-0.8	50
0.8-0.85	19
0.85-0.9	10
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC314679
0.9535	High Similarity	NPC21844
0.9318	High Similarity	NPC477878
0.9318	High Similarity	NPC324793
0.881	High Similarity	NPC325452
0.881	High Similarity	NPC248763
0.878	High Similarity	NPC154186
0.878	High Similarity	NPC279026
0.878	High Similarity	NPC201844
0.878	High Similarity	NPC261080
0.878	High Similarity	NPC301585
0.878	High Similarity	NPC301696
0.878	High Similarity	NPC14227
0.878	High Similarity	NPC113928
0.8372	Intermediate Similarity	NPC171736
0.8372	Intermediate Similarity	NPC216630
0.8372	Intermediate Similarity	NPC307783
0.8372	Intermediate Similarity	NPC196924
0.8372	Intermediate Similarity	NPC209970
0.8372	Intermediate Similarity	NPC149184
0.8367	Intermediate Similarity	NPC72722
0.8333	Intermediate Similarity	NPC3531
0.8333	Intermediate Similarity	NPC183424
0.8333	Intermediate Similarity	NPC118968
0.8333	Intermediate Similarity	NPC294085
0.8333	Intermediate Similarity	NPC214610
0.8293	Intermediate Similarity	NPC252843
0.8182	Intermediate Similarity	NPC67462
0.8095	Intermediate Similarity	NPC268826
0.8049	Intermediate Similarity	NPC155263
0.8	Intermediate Similarity	NPC19305
0.8	Intermediate Similarity	NPC74845
0.8	Intermediate Similarity	NPC255837
0.7826	Intermediate Similarity	NPC8219
0.7805	Intermediate Similarity	NPC156630
0.7755	Intermediate Similarity	NPC305182
0.7674	Intermediate Similarity	NPC54980
0.7674	Intermediate Similarity	NPC305660
0.7674	Intermediate Similarity	NPC201622
0.7674	Intermediate Similarity	NPC22903
0.766	Intermediate Similarity	NPC12438
0.766	Intermediate Similarity	NPC30195
0.7619	Intermediate Similarity	NPC134782
0.76	Intermediate Similarity	NPC314084
0.7556	Intermediate Similarity	NPC163746
0.7556	Intermediate Similarity	NPC103286
0.75	Intermediate Similarity	NPC328497
0.75	Intermediate Similarity	NPC324004
0.75	Intermediate Similarity	NPC249754
0.75	Intermediate Similarity	NPC219536
0.75	Intermediate Similarity	NPC31551
0.7455	Intermediate Similarity	NPC470363
0.7455	Intermediate Similarity	NPC475821
0.7391	Intermediate Similarity	NPC71317
0.7391	Intermediate Similarity	NPC129972
0.7391	Intermediate Similarity	NPC301528
0.7347	Intermediate Similarity	NPC106872
0.7347	Intermediate Similarity	NPC131770
0.7347	Intermediate Similarity	NPC200618
0.7333	Intermediate Similarity	NPC28598
0.7333	Intermediate Similarity	NPC12156
0.7333	Intermediate Similarity	NPC161097
0.7333	Intermediate Similarity	NPC250028
0.7333	Intermediate Similarity	NPC40597
0.7333	Intermediate Similarity	NPC256163
0.7333	Intermediate Similarity	NPC149299
0.7317	Intermediate Similarity	NPC175342
0.7273	Intermediate Similarity	NPC73245
0.7234	Intermediate Similarity	NPC317128
0.72	Intermediate Similarity	NPC476469
0.72	Intermediate Similarity	NPC304162
0.7174	Intermediate Similarity	NPC53541
0.717	Intermediate Similarity	NPC319589
0.7143	Intermediate Similarity	NPC469924
0.7111	Intermediate Similarity	NPC223249
0.7111	Intermediate Similarity	NPC80234
0.7069	Intermediate Similarity	NPC474552
0.7059	Intermediate Similarity	NPC90904
0.7021	Intermediate Similarity	NPC289686
0.7021	Intermediate Similarity	NPC236579
0.7021	Intermediate Similarity	NPC203531
0.7018	Intermediate Similarity	NPC469921
0.7	Intermediate Similarity	NPC13105
0.7	Intermediate Similarity	NPC180534
0.6957	Remote Similarity	NPC165533
0.6949	Remote Similarity	NPC470325
0.6949	Remote Similarity	NPC53642
0.6949	Remote Similarity	NPC234767
0.6949	Remote Similarity	NPC314103
0.6939	Remote Similarity	NPC282440
0.6939	Remote Similarity	NPC166287
0.6939	Remote Similarity	NPC308301
0.6923	Remote Similarity	NPC470412
0.6923	Remote Similarity	NPC470410
0.6905	Remote Similarity	NPC18224
0.6905	Remote Similarity	NPC328710
0.6897	Remote Similarity	NPC125312
0.6897	Remote Similarity	NPC174560
0.6897	Remote Similarity	NPC469923
0.6889	Remote Similarity	NPC38930
0.6889	Remote Similarity	NPC325454
0.6875	Remote Similarity	NPC76051
0.6863	Remote Similarity	NPC26253
0.6852	Remote Similarity	NPC87394
0.6833	Remote Similarity	NPC469791
0.6833	Remote Similarity	NPC476330
0.6833	Remote Similarity	NPC19311
0.6833	Remote Similarity	NPC230047
0.6792	Remote Similarity	NPC281245
0.678	Remote Similarity	NPC235788
0.6739	Remote Similarity	NPC81263
0.6735	Remote Similarity	NPC47363
0.6735	Remote Similarity	NPC287231
0.6735	Remote Similarity	NPC469781
0.6731	Remote Similarity	NPC50457
0.6724	Remote Similarity	NPC302188
0.6721	Remote Similarity	NPC477931
0.6721	Remote Similarity	NPC268736
0.6721	Remote Similarity	NPC241949
0.6721	Remote Similarity	NPC42060
0.6667	Remote Similarity	NPC158179
0.6667	Remote Similarity	NPC109026
0.6667	Remote Similarity	NPC177022
0.6667	Remote Similarity	NPC294548
0.6667	Remote Similarity	NPC14608
0.6667	Remote Similarity	NPC139029
0.6667	Remote Similarity	NPC69245
0.6667	Remote Similarity	NPC1813
0.6667	Remote Similarity	NPC280532
0.6667	Remote Similarity	NPC36061
0.6613	Remote Similarity	NPC41542
0.6613	Remote Similarity	NPC474221
0.6613	Remote Similarity	NPC476626
0.6613	Remote Similarity	NPC286842
0.6613	Remote Similarity	NPC130459
0.6613	Remote Similarity	NPC472875
0.6613	Remote Similarity	NPC478180
0.6604	Remote Similarity	NPC100096
0.66	Remote Similarity	NPC52700
0.66	Remote Similarity	NPC63182
0.66	Remote Similarity	NPC145045
0.66	Remote Similarity	NPC105329
0.6591	Remote Similarity	NPC317203
0.6585	Remote Similarity	NPC174368
0.6585	Remote Similarity	NPC61066
0.6585	Remote Similarity	NPC122768
0.6585	Remote Similarity	NPC151140
0.6585	Remote Similarity	NPC104195
0.6552	Remote Similarity	NPC226602
0.6552	Remote Similarity	NPC472019
0.6552	Remote Similarity	NPC472020
0.6545	Remote Similarity	NPC32467
0.6545	Remote Similarity	NPC85813
0.6545	Remote Similarity	NPC53463
0.6545	Remote Similarity	NPC25417
0.6545	Remote Similarity	NPC290563
0.6545	Remote Similarity	NPC281972
0.6545	Remote Similarity	NPC88966
0.6545	Remote Similarity	NPC87564
0.6545	Remote Similarity	NPC6095
0.6545	Remote Similarity	NPC23155
0.6545	Remote Similarity	NPC154245
0.6545	Remote Similarity	NPC261831
0.6545	Remote Similarity	NPC424
0.6545	Remote Similarity	NPC320588
0.6545	Remote Similarity	NPC469937
0.6522	Remote Similarity	NPC316546
0.6522	Remote Similarity	NPC326532
0.6522	Remote Similarity	NPC223315
0.6508	Remote Similarity	NPC281203
0.6508	Remote Similarity	NPC476614
0.6508	Remote Similarity	NPC82315
0.6508	Remote Similarity	NPC469724
0.6508	Remote Similarity	NPC290445
0.6508	Remote Similarity	NPC319007
0.6508	Remote Similarity	NPC31187
0.6508	Remote Similarity	NPC36616
0.6508	Remote Similarity	NPC470956
0.6508	Remote Similarity	NPC100917
0.6508	Remote Similarity	NPC476629
0.6491	Remote Similarity	NPC319279
0.6481	Remote Similarity	NPC18357
0.6471	Remote Similarity	NPC326957
0.6452	Remote Similarity	NPC308294
0.6452	Remote Similarity	NPC142423
0.6444	Remote Similarity	NPC80641
0.6444	Remote Similarity	NPC328441
0.6444	Remote Similarity	NPC154642
0.6444	Remote Similarity	NPC80396
0.6441	Remote Similarity	NPC478126
0.6441	Remote Similarity	NPC472328
0.6441	Remote Similarity	NPC40206
0.6441	Remote Similarity	NPC472021
0.6406	Remote Similarity	NPC98711
0.6406	Remote Similarity	NPC64466
0.6406	Remote Similarity	NPC196197
0.6406	Remote Similarity	NPC67608
0.6406	Remote Similarity	NPC252032
0.6406	Remote Similarity	NPC476734
0.6406	Remote Similarity	NPC469941

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 NPC55023 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	864
0.1-0.2	4736
0.2-0.3	2302
0.3-0.4	838
0.4-0.5	298
0.5-0.6	74
0.6-0.7	20
0.7-0.8	10
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9762	High Similarity	NPD634	Phase 3
0.878	High Similarity	NPD633	Phase 3
0.878	High Similarity	NPD9448	Phase 2
0.8605	High Similarity	NPD387	Clinical (unspecified phase)
0.8542	High Similarity	NPD3186	Phase 1
0.8372	Intermediate Similarity	NPD2270	Approved
0.8333	Intermediate Similarity	NPD9655	Approved
0.8333	Intermediate Similarity	NPD9450	Approved
0.8333	Intermediate Similarity	NPD77	Approved
0.82	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD9449	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3206	Approved
0.76	Intermediate Similarity	NPD9638	Phase 2
0.7455	Intermediate Similarity	NPD3198	Approved
0.7381	Intermediate Similarity	NPD9447	Approved
0.7333	Intermediate Similarity	NPD9635	Discontinued
0.7	Intermediate Similarity	NPD2266	Phase 2
0.7	Intermediate Similarity	NPD622	Approved
0.6949	Remote Similarity	NPD7909	Approved
0.6939	Remote Similarity	NPD9431	Approved
0.6939	Remote Similarity	NPD9430	Approved
0.6897	Remote Similarity	NPD9676	Phase 3
0.6735	Remote Similarity	NPD2699	Approved
0.6724	Remote Similarity	NPD9656	Approved
0.6721	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD3172	Approved
0.6545	Remote Similarity	NPD4266	Approved
0.6545	Remote Similarity	NPD3730	Approved
0.6545	Remote Similarity	NPD3194	Approved
0.6545	Remote Similarity	NPD3195	Phase 2
0.6545	Remote Similarity	NPD3728	Approved
0.6545	Remote Similarity	NPD3196	Approved
0.6522	Remote Similarity	NPD9513	Phase 1
0.6491	Remote Similarity	NPD9438	Approved
0.6491	Remote Similarity	NPD9439	Approved
0.6452	Remote Similarity	NPD375	Phase 2
0.6429	Remote Similarity	NPD9454	Approved
0.6212	Remote Similarity	NPD6081	Approved
0.6038	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7341	Phase 2
0.6032	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6	Remote Similarity	NPD29	Approved
0.6	Remote Similarity	NPD28	Approved
0.6	Remote Similarity	NPD8857	Approved
0.5962	Remote Similarity	NPD386	Approved
0.5962	Remote Similarity	NPD388	Approved
0.5942	Remote Similarity	NPD2257	Approved
0.5942	Remote Similarity	NPD3702	Approved
0.5926	Remote Similarity	NPD3173	Approved
0.5882	Remote Similarity	NPD8975	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD6117	Approved
0.58	Remote Similarity	NPD9116	Phase 1
0.5775	Remote Similarity	NPD6116	Phase 1
0.5769	Remote Similarity	NPD8974	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5360	Phase 3
0.5758	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD9441	Phase 2
0.5694	Remote Similarity	NPD6697	Approved
0.5694	Remote Similarity	NPD4238	Approved
0.5694	Remote Similarity	NPD4802	Phase 2
0.5694	Remote Similarity	NPD6118	Approved
0.5694	Remote Similarity	NPD6115	Approved
0.5694	Remote Similarity	NPD6114	Approved
0.5692	Remote Similarity	NPD9421	Phase 1
0.5692	Remote Similarity	NPD7331	Phase 2
0.5686	Remote Similarity	NPD1462	Approved
0.5672	Remote Similarity	NPD3698	Phase 2
0.5672	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD3725	Approved
0.5672	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD3726	Approved
0.5636	Remote Similarity	NPD9018	Approved
0.5625	Remote Similarity	NPD3197	Phase 1
0.56	Remote Similarity	NPD1460	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