NPASS Compound

Structure

NPC470394 OpenBabel07101718312D 22 22 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 3 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 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 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 17 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 19 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	309.23
Volume:	340.786
LogP:	2.931
LogD:	2.787
LogS:	-3.071
# Rotatable Bonds:	12
TPSA:	73.58
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	2.858
Fsp3:	0.722
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	2.5217797883669846e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	74.36233520507812%
Volume Distribution (VD):	1.619
Pgp-substrate:	17.307126998901367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.2
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.581
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	10.834
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.324
Skin Sensitization:	0.935
Carcinogencity:	0.067
Eye Corrosion:	0.011
Eye Irritation:	0.272
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC470394

Natural Product ID:	NPC470394
*Common Name:**	12-(5-Hydroxy-6-Methylpyridin-2-Yl)Dodecane-1,6-Diol
IUPAC Name:	12-(5-hydroxy-6-methylpyridin-2-yl)dodecane-1,6-diol
Synonyms:	12'-hydroxy-7'-multijuguinol
Standard InCHIKey:	NVCDYIVRRNILOL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H31NO3/c1-15-18(22)13-12-16(19-15)9-5-2-3-6-10-17(21)11-7-4-8-14-20/h12-13,17,20-22H,2-11,14H2,1H3
SMILES:	OCCCCCC(CCCCCCc1ccc(c(n1)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022770
PubChem CID:	57382622
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004152] Methylpyridines

*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
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20000694]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22304303]
NPO9634	Senna multijuga	Species	Fabaceae	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
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	MIC	=	1.5	ug	PMID[543979]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	51.0	%	PMID[543979]

☑ 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 NPC470394 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	273
0.1-0.2	3928
0.2-0.3	13221
0.3-0.4	12847
0.4-0.5	8709
0.5-0.6	3058
0.6-0.7	564
0.7-0.8	86
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470403
1.0	High Similarity	NPC470404
0.9853	High Similarity	NPC470395
0.9366	High Similarity	NPC284348
0.9155	High Similarity	NPC257142
0.86	High Similarity	NPC116573
0.8581	High Similarity	NPC153769
0.8562	High Similarity	NPC220523
0.8435	Intermediate Similarity	NPC161292
0.8217	Intermediate Similarity	NPC44161
0.8054	Intermediate Similarity	NPC471598
0.7917	Intermediate Similarity	NPC174421
0.7818	Intermediate Similarity	NPC478032
0.7785	Intermediate Similarity	NPC280853
0.7756	Intermediate Similarity	NPC63562
0.7736	Intermediate Similarity	NPC79911
0.7733	Intermediate Similarity	NPC245657
0.7733	Intermediate Similarity	NPC285016
0.7733	Intermediate Similarity	NPC318935
0.7722	Intermediate Similarity	NPC84508
0.7718	Intermediate Similarity	NPC471596
0.7682	Intermediate Similarity	NPC60553
0.7673	Intermediate Similarity	NPC25899
0.7673	Intermediate Similarity	NPC120798
0.7661	Intermediate Similarity	NPC3715
0.7658	Intermediate Similarity	NPC269919
0.7658	Intermediate Similarity	NPC132680
0.7636	Intermediate Similarity	NPC194724
0.7607	Intermediate Similarity	NPC473764
0.7607	Intermediate Similarity	NPC314940
0.7574	Intermediate Similarity	NPC320394
0.7562	Intermediate Similarity	NPC63338
0.7562	Intermediate Similarity	NPC324203
0.7562	Intermediate Similarity	NPC322976
0.756	Intermediate Similarity	NPC219963
0.7516	Intermediate Similarity	NPC48192
0.75	Intermediate Similarity	NPC126481
0.7485	Intermediate Similarity	NPC314573
0.7483	Intermediate Similarity	NPC471594
0.7469	Intermediate Similarity	NPC263439
0.7469	Intermediate Similarity	NPC118511
0.7455	Intermediate Similarity	NPC252590
0.7427	Intermediate Similarity	NPC42591
0.7399	Intermediate Similarity	NPC110741
0.7381	Intermediate Similarity	NPC283152
0.7365	Intermediate Similarity	NPC95898
0.7362	Intermediate Similarity	NPC211187
0.7358	Intermediate Similarity	NPC26872
0.7358	Intermediate Similarity	NPC36168
0.7353	Intermediate Similarity	NPC266551
0.7353	Intermediate Similarity	NPC161887
0.7351	Intermediate Similarity	NPC328029
0.7349	Intermediate Similarity	NPC253810
0.733	Intermediate Similarity	NPC226202
0.7301	Intermediate Similarity	NPC47298
0.7301	Intermediate Similarity	NPC315214
0.7279	Intermediate Similarity	NPC278451
0.726	Intermediate Similarity	NPC151489
0.7256	Intermediate Similarity	NPC159319
0.7256	Intermediate Similarity	NPC32028
0.7232	Intermediate Similarity	NPC230403
0.7222	Intermediate Similarity	NPC26850
0.7212	Intermediate Similarity	NPC471178
0.7208	Intermediate Similarity	NPC85443
0.7195	Intermediate Similarity	NPC124542
0.7195	Intermediate Similarity	NPC59779
0.7195	Intermediate Similarity	NPC471177
0.7195	Intermediate Similarity	NPC177404
0.7186	Intermediate Similarity	NPC256828
0.7152	Intermediate Similarity	NPC473057
0.7143	Intermediate Similarity	NPC158129
0.7126	Intermediate Similarity	NPC20249
0.7101	Intermediate Similarity	NPC259545
0.7101	Intermediate Similarity	NPC471294
0.7072	Intermediate Similarity	NPC472284
0.7069	Intermediate Similarity	NPC62069
0.7066	Intermediate Similarity	NPC108469
0.7062	Intermediate Similarity	NPC144381
0.7052	Intermediate Similarity	NPC118776
0.7043	Intermediate Similarity	NPC316403
0.7041	Intermediate Similarity	NPC121658
0.7041	Intermediate Similarity	NPC14651
0.7035	Intermediate Similarity	NPC472168
0.7033	Intermediate Similarity	NPC18487
0.7029	Intermediate Similarity	NPC241025
0.7029	Intermediate Similarity	NPC255721
0.7024	Intermediate Similarity	NPC1527
0.7018	Intermediate Similarity	NPC203754
0.7018	Intermediate Similarity	NPC288943
0.7018	Intermediate Similarity	NPC150048
0.7006	Intermediate Similarity	NPC230805
0.6994	Remote Similarity	NPC325705
0.6994	Remote Similarity	NPC52831
0.6982	Remote Similarity	NPC476518
0.6959	Remote Similarity	NPC312872
0.6951	Remote Similarity	NPC477889
0.6949	Remote Similarity	NPC66083
0.6943	Remote Similarity	NPC314270
0.6936	Remote Similarity	NPC232340
0.6935	Remote Similarity	NPC118832
0.6935	Remote Similarity	NPC47059
0.6935	Remote Similarity	NPC329708
0.6935	Remote Similarity	NPC264166
0.6935	Remote Similarity	NPC274291
0.6935	Remote Similarity	NPC165349
0.6915	Remote Similarity	NPC477111
0.6907	Remote Similarity	NPC313804
0.6907	Remote Similarity	NPC315804
0.6902	Remote Similarity	NPC249040
0.6901	Remote Similarity	NPC474409
0.6898	Remote Similarity	NPC472286
0.6898	Remote Similarity	NPC472287
0.6898	Remote Similarity	NPC471736
0.6897	Remote Similarity	NPC478023
0.6897	Remote Similarity	NPC249662
0.6893	Remote Similarity	NPC194040
0.6884	Remote Similarity	NPC76327
0.6882	Remote Similarity	NPC317572
0.6866	Remote Similarity	NPC213774
0.686	Remote Similarity	NPC303225
0.6857	Remote Similarity	NPC314394
0.6851	Remote Similarity	NPC79293
0.6851	Remote Similarity	NPC279401
0.6848	Remote Similarity	NPC128823
0.6848	Remote Similarity	NPC476167
0.6845	Remote Similarity	NPC470500
0.6845	Remote Similarity	NPC137929
0.6845	Remote Similarity	NPC164374
0.6842	Remote Similarity	NPC5145
0.6839	Remote Similarity	NPC88363
0.6839	Remote Similarity	NPC477110
0.6826	Remote Similarity	NPC285635
0.6821	Remote Similarity	NPC134586
0.6818	Remote Similarity	NPC133306
0.6816	Remote Similarity	NPC183805
0.6802	Remote Similarity	NPC111624
0.6796	Remote Similarity	NPC280964
0.6796	Remote Similarity	NPC114335
0.6796	Remote Similarity	NPC141915
0.6793	Remote Similarity	NPC192315
0.6789	Remote Similarity	NPC469589
0.6782	Remote Similarity	NPC211997
0.6765	Remote Similarity	NPC41717
0.6761	Remote Similarity	NPC144114
0.6753	Remote Similarity	NPC256893
0.6748	Remote Similarity	NPC288445
0.6744	Remote Similarity	NPC476686
0.6744	Remote Similarity	NPC105758
0.6744	Remote Similarity	NPC476688
0.6743	Remote Similarity	NPC42979
0.6743	Remote Similarity	NPC72980
0.6742	Remote Similarity	NPC94943
0.6742	Remote Similarity	NPC295158
0.6742	Remote Similarity	NPC314002
0.674	Remote Similarity	NPC469390
0.6738	Remote Similarity	NPC66815
0.6728	Remote Similarity	NPC302159
0.6726	Remote Similarity	NPC322644
0.6725	Remote Similarity	NPC278874
0.6724	Remote Similarity	NPC224764
0.6722	Remote Similarity	NPC246700
0.6722	Remote Similarity	NPC128751
0.672	Remote Similarity	NPC477113
0.6711	Remote Similarity	NPC471311
0.6711	Remote Similarity	NPC471313
0.6711	Remote Similarity	NPC165370
0.6708	Remote Similarity	NPC471323
0.6705	Remote Similarity	NPC168486
0.6705	Remote Similarity	NPC34508
0.6705	Remote Similarity	NPC222592
0.6704	Remote Similarity	NPC171171
0.6686	Remote Similarity	NPC184964
0.6686	Remote Similarity	NPC224632
0.6685	Remote Similarity	NPC190007
0.6685	Remote Similarity	NPC207851
0.6685	Remote Similarity	NPC469497
0.6685	Remote Similarity	NPC106833
0.6685	Remote Similarity	NPC204717
0.6667	Remote Similarity	NPC244536
0.6667	Remote Similarity	NPC45850
0.6667	Remote Similarity	NPC36498
0.6667	Remote Similarity	NPC477891
0.6649	Remote Similarity	NPC471080
0.6649	Remote Similarity	NPC469592
0.6649	Remote Similarity	NPC474188
0.6649	Remote Similarity	NPC267928
0.6649	Remote Similarity	NPC308392
0.6647	Remote Similarity	NPC141353
0.6647	Remote Similarity	NPC258773
0.6632	Remote Similarity	NPC304183
0.6632	Remote Similarity	NPC475841
0.6632	Remote Similarity	NPC474145
0.6632	Remote Similarity	NPC472111
0.6629	Remote Similarity	NPC220765
0.6629	Remote Similarity	NPC212535
0.662	Remote Similarity	NPC9336
0.6614	Remote Similarity	NPC475774
0.6614	Remote Similarity	NPC223427
0.6612	Remote Similarity	NPC99666
0.6611	Remote Similarity	NPC61350

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 NPC470394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	771
0.2-0.3	864
0.3-0.4	1662
0.4-0.5	3493
0.5-0.6	1833
0.6-0.7	314
0.7-0.8	27
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8867	High Similarity	NPD863	Approved
0.8867	High Similarity	NPD861	Approved
0.8867	High Similarity	NPD862	Approved
0.8478	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3525	Discontinued
0.7914	Intermediate Similarity	NPD6159	Phase 2
0.7771	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD9382	Approved
0.7658	Intermediate Similarity	NPD9383	Approved
0.7614	Intermediate Similarity	NPD2175	Phase 3
0.7614	Intermediate Similarity	NPD2176	Approved
0.7614	Intermediate Similarity	NPD2177	Approved
0.7562	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2383	Phase 1
0.7365	Intermediate Similarity	NPD158	Discontinued
0.7365	Intermediate Similarity	NPD9690	Approved
0.7356	Intermediate Similarity	NPD5316	Approved
0.7349	Intermediate Similarity	NPD2123	Phase 3
0.7301	Intermediate Similarity	NPD1684	Approved
0.7301	Intermediate Similarity	NPD1685	Approved
0.7284	Intermediate Similarity	NPD5255	Approved
0.7255	Intermediate Similarity	NPD9076	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD9705	Discontinued
0.7239	Intermediate Similarity	NPD112	Approved
0.7228	Intermediate Similarity	NPD6290	Phase 2
0.7186	Intermediate Similarity	NPD565	Phase 2
0.7166	Intermediate Similarity	NPD5939	Approved
0.7166	Intermediate Similarity	NPD5936	Approved
0.7166	Intermediate Similarity	NPD4502	Phase 2
0.7151	Intermediate Similarity	NPD4203	Approved
0.7151	Intermediate Similarity	NPD4204	Approved
0.7143	Intermediate Similarity	NPD852	Discontinued
0.7126	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6158	Phase 2
0.7045	Intermediate Similarity	NPD1034	Phase 3
0.7045	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9695	Approved
0.7018	Intermediate Similarity	NPD2381	Approved
0.7018	Intermediate Similarity	NPD2380	Approved
0.7018	Intermediate Similarity	NPD2382	Approved
0.7017	Intermediate Similarity	NPD1229	Phase 2
0.7012	Intermediate Similarity	NPD2582	Approved
0.7012	Intermediate Similarity	NPD2581	Approved
0.7011	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD408	Approved
0.7	Intermediate Similarity	NPD6590	Discontinued
0.6994	Remote Similarity	NPD9510	Approved
0.6982	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2882	Phase 1
0.6966	Remote Similarity	NPD1213	Phase 3
0.6961	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3477	Phase 2
0.6936	Remote Similarity	NPD3920	Phase 2
0.6935	Remote Similarity	NPD4122	Approved
0.6935	Remote Similarity	NPD31	Approved
0.6935	Remote Similarity	NPD4035	Approved
0.6935	Remote Similarity	NPD4033	Approved
0.6935	Remote Similarity	NPD4036	Approved
0.6935	Remote Similarity	NPD4034	Approved
0.6935	Remote Similarity	NPD4037	Approved
0.6935	Remote Similarity	NPD32	Approved
0.6935	Remote Similarity	NPD4039	Approved
0.6935	Remote Similarity	NPD4038	Approved
0.6932	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2781	Approved
0.6914	Remote Similarity	NPD5596	Phase 2
0.6905	Remote Similarity	NPD926	Approved
0.6905	Remote Similarity	NPD2782	Approved
0.6905	Remote Similarity	NPD925	Approved
0.6905	Remote Similarity	NPD2780	Approved
0.6893	Remote Similarity	NPD5256	Discontinued
0.6889	Remote Similarity	NPD6569	Phase 2
0.6884	Remote Similarity	NPD9507	Approved
0.6871	Remote Similarity	NPD9596	Approved
0.6871	Remote Similarity	NPD9595	Approved
0.6868	Remote Similarity	NPD5512	Phase 3
0.6864	Remote Similarity	NPD424	Approved
0.6864	Remote Similarity	NPD425	Approved
0.6856	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3717	Discontinued
0.6839	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD9689	Approved
0.6793	Remote Similarity	NPD2727	Phase 2
0.6793	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1592	Phase 3
0.6776	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6550	Discontinued
0.6772	Remote Similarity	NPD7222	Phase 2
0.6761	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7726	Phase 1
0.6739	Remote Similarity	NPD6988	Phase 1
0.6738	Remote Similarity	NPD9376	Approved
0.6736	Remote Similarity	NPD9342	Approved
0.6726	Remote Similarity	NPD1418	Phase 2
0.6721	Remote Similarity	NPD3396	Approved
0.6721	Remote Similarity	NPD3395	Approved
0.6717	Remote Similarity	NPD8356	Approved
0.6711	Remote Similarity	NPD522	Approved
0.6705	Remote Similarity	NPD2077	Approved
0.6705	Remote Similarity	NPD2076	Approved
0.6703	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4702	Approved
0.6687	Remote Similarity	NPD4703	Approved
0.6686	Remote Similarity	NPD7474	Suspended
0.6686	Remote Similarity	NPD5320	Approved
0.6686	Remote Similarity	NPD5319	Approved
0.6685	Remote Similarity	NPD8063	Discontinued
0.6685	Remote Similarity	NPD3321	Discontinued
0.6667	Remote Similarity	NPD9363	Approved
0.6667	Remote Similarity	NPD4086	Phase 1
0.6667	Remote Similarity	NPD1768	Approved
0.6667	Remote Similarity	NPD9364	Phase 2
0.6667	Remote Similarity	NPD5420	Discontinued
0.6648	Remote Similarity	NPD3082	Discontinued
0.6648	Remote Similarity	NPD2762	Phase 2
0.6646	Remote Similarity	NPD9506	Approved
0.6632	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7418	Discontinued
0.6605	Remote Similarity	NPD3813	Approved
0.6601	Remote Similarity	NPD9284	Approved
0.6597	Remote Similarity	NPD5429	Discontinued
0.6597	Remote Similarity	NPD7452	Approved
0.6597	Remote Similarity	NPD7453	Approved
0.6591	Remote Similarity	NPD6642	Approved
0.6591	Remote Similarity	NPD6641	Approved
0.6584	Remote Similarity	NPD8430	Approved
0.6584	Remote Similarity	NPD4805	Approved
0.6578	Remote Similarity	NPD9687	Approved
0.6578	Remote Similarity	NPD9688	Approved
0.6573	Remote Similarity	NPD3386	Phase 2
0.6571	Remote Similarity	NPD6492	Phase 2
0.657	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6283	Phase 2
0.6559	Remote Similarity	NPD2952	Discontinued
0.6557	Remote Similarity	NPD4699	Discontinued
0.6556	Remote Similarity	NPD6227	Discontinued
0.6556	Remote Similarity	NPD4889	Approved
0.6554	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.655	Remote Similarity	NPD444	Approved
0.655	Remote Similarity	NPD5140	Approved
0.655	Remote Similarity	NPD5138	Approved
0.6548	Remote Similarity	NPD5164	Discontinued
0.6546	Remote Similarity	NPD5416	Discontinued
0.6545	Remote Similarity	NPD3003	Approved
0.6543	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD313	Approved
0.6522	Remote Similarity	NPD3923	Approved
0.6522	Remote Similarity	NPD3921	Approved
0.6522	Remote Similarity	NPD3922	Approved
0.6522	Remote Similarity	NPD1649	Discontinued
0.6522	Remote Similarity	NPD3924	Approved
0.6519	Remote Similarity	NPD4375	Approved
0.6519	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1352	Discontinued
0.6503	Remote Similarity	NPD8823	Approved
0.65	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5999	Phase 2
0.6486	Remote Similarity	NPD4526	Approved
0.6486	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4528	Approved
0.6486	Remote Similarity	NPD4529	Approved
0.6482	Remote Similarity	NPD3875	Discontinued
0.6481	Remote Similarity	NPD5020	Approved
0.648	Remote Similarity	NPD2615	Phase 3
0.648	Remote Similarity	NPD2616	Phase 3
0.6474	Remote Similarity	NPD3931	Approved
0.6474	Remote Similarity	NPD3928	Approved
0.6471	Remote Similarity	NPD7948	Phase 1
0.6471	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4804	Approved
0.6458	Remote Similarity	NPD5530	Phase 1
0.6457	Remote Similarity	NPD9548	Phase 2
0.6457	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5100	Phase 3
0.6437	Remote Similarity	NPD5862	Discovery
0.6432	Remote Similarity	NPD4372	Phase 1
0.6429	Remote Similarity	NPD4927	Discontinued
0.6425	Remote Similarity	NPD1392	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