NPASS Compound

Structure

NPC196407 OpenBabel07101718182D 25 27 0 0 1 0 0 0 0 0999 V2000 -1.9487 -4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9128 -3.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5134 1.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5468 -4.2024 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 -4.5468 -3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 -4.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 24 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 1 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 21 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	368.081
LogP:	4.523
LogD:	4.189
LogS:	-4.615
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.826
Synthetic Accessibility Score:	4.482
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924
MDCK Permeability:	2.5294417355326004e-05
Pgp-inhibitor:	0.487
Pgp-substrate:	0.167
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	95.15352630615234%
Volume Distribution (VD):	0.977
Pgp-substrate:	5.5909504890441895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.8
CYP2C19-inhibitor:	0.432
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.455
CYP2C9-substrate:	0.557
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.767
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.589

ADMET: Excretion

Clearance (CL):	13.702
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.568
Drug-inuced Liver Injury (DILI):	0.319
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.411
Skin Sensitization:	0.63
Carcinogencity:	0.755
Eye Corrosion:	0.07
Eye Irritation:	0.079
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC196407

Natural Product ID:	NPC196407
*Common Name:**	Spicatanol Methyl Ether
IUPAC Name:	(2R)-3-[(E)-2-[(1S,4aS,8aR)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2-methoxy-2H-furan-5-one
Synonyms:	Spicatanol methyl ether
Standard InCHIKey:	ILKIVDALMQTOOO-XYSGFGBLSA-N
Standard InCHI:	InChI=1S/C21H28O4/c1-13-11-16(22)18-20(2,3)9-6-10-21(18,4)15(13)8-7-14-12-17(23)25-19(14)24-5/h7-8,11-12,15,18-19H,6,9-10H2,1-5H3/b8-7+/t15-,18-,19+,21+/m0/s1
SMILES:	CC1=CC(=O)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1/C=C/C1=CC(=O)O[C@H]1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467052
PubChem CID:	44574437
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	54.1	%	PMID[570809]

☑ 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 NPC196407 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	198
0.1-0.2	1254
0.2-0.3	5327
0.3-0.4	13545
0.4-0.5	11421
0.5-0.6	7851
0.6-0.7	2696
0.7-0.8	373
0.8-0.85	24
0.85-0.9	2
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC242069
0.931	High Similarity	NPC469939
0.9268	High Similarity	NPC268122
0.9157	High Similarity	NPC118423
0.9059	High Similarity	NPC168248
0.881	High Similarity	NPC94200
0.8587	High Similarity	NPC112654
0.8391	Intermediate Similarity	NPC470800
0.8391	Intermediate Similarity	NPC71626
0.8352	Intermediate Similarity	NPC65513
0.8333	Intermediate Similarity	NPC474844
0.8333	Intermediate Similarity	NPC284561
0.8295	Intermediate Similarity	NPC189311
0.828	Intermediate Similarity	NPC295347
0.8276	Intermediate Similarity	NPC474790
0.8276	Intermediate Similarity	NPC474976
0.8247	Intermediate Similarity	NPC471365
0.8247	Intermediate Similarity	NPC132395
0.8247	Intermediate Similarity	NPC471364
0.8193	Intermediate Similarity	NPC65650
0.8191	Intermediate Similarity	NPC311166
0.8125	Intermediate Similarity	NPC477720
0.8105	Intermediate Similarity	NPC208094
0.8095	Intermediate Similarity	NPC4509
0.809	Intermediate Similarity	NPC472442
0.809	Intermediate Similarity	NPC329630
0.8068	Intermediate Similarity	NPC193198
0.8068	Intermediate Similarity	NPC472440
0.8043	Intermediate Similarity	NPC220454
0.8043	Intermediate Similarity	NPC212679
0.8043	Intermediate Similarity	NPC469595
0.8022	Intermediate Similarity	NPC472302
0.8	Intermediate Similarity	NPC220478
0.7979	Intermediate Similarity	NPC477129
0.7979	Intermediate Similarity	NPC477130
0.7979	Intermediate Similarity	NPC38830
0.7979	Intermediate Similarity	NPC88507
0.7957	Intermediate Similarity	NPC141831
0.7935	Intermediate Similarity	NPC5509
0.7917	Intermediate Similarity	NPC204054
0.7917	Intermediate Similarity	NPC257726
0.7912	Intermediate Similarity	NPC163016
0.7912	Intermediate Similarity	NPC75315
0.79	Intermediate Similarity	NPC127790
0.7895	Intermediate Similarity	NPC473369
0.7895	Intermediate Similarity	NPC209355
0.7889	Intermediate Similarity	NPC471300
0.7889	Intermediate Similarity	NPC474860
0.7865	Intermediate Similarity	NPC469
0.7857	Intermediate Similarity	NPC20025
0.7849	Intermediate Similarity	NPC232426
0.7849	Intermediate Similarity	NPC469372
0.7849	Intermediate Similarity	NPC281942
0.7849	Intermediate Similarity	NPC477782
0.7826	Intermediate Similarity	NPC226863
0.7816	Intermediate Similarity	NPC471299
0.7812	Intermediate Similarity	NPC319692
0.7812	Intermediate Similarity	NPC325960
0.7802	Intermediate Similarity	NPC211892
0.7789	Intermediate Similarity	NPC474554
0.7778	Intermediate Similarity	NPC149869
0.7766	Intermediate Similarity	NPC477783
0.7753	Intermediate Similarity	NPC200513
0.7753	Intermediate Similarity	NPC16321
0.7742	Intermediate Similarity	NPC251528
0.7738	Intermediate Similarity	NPC276336
0.7732	Intermediate Similarity	NPC110937
0.7717	Intermediate Similarity	NPC181327
0.7717	Intermediate Similarity	NPC475678
0.7701	Intermediate Similarity	NPC471220
0.7684	Intermediate Similarity	NPC475657
0.7684	Intermediate Similarity	NPC166346
0.7684	Intermediate Similarity	NPC471571
0.7677	Intermediate Similarity	NPC473384
0.7674	Intermediate Similarity	NPC27205
0.7667	Intermediate Similarity	NPC22611
0.7653	Intermediate Similarity	NPC474440
0.764	Intermediate Similarity	NPC282293
0.764	Intermediate Similarity	NPC149237
0.7634	Intermediate Similarity	NPC215831
0.7634	Intermediate Similarity	NPC474629
0.7634	Intermediate Similarity	NPC477128
0.7629	Intermediate Similarity	NPC240673
0.7629	Intermediate Similarity	NPC17578
0.7609	Intermediate Similarity	NPC474062
0.7609	Intermediate Similarity	NPC472863
0.7604	Intermediate Similarity	NPC470255
0.76	Intermediate Similarity	NPC134077
0.7586	Intermediate Similarity	NPC316500
0.7582	Intermediate Similarity	NPC30486
0.7582	Intermediate Similarity	NPC475100
0.7579	Intermediate Similarity	NPC179517
0.7579	Intermediate Similarity	NPC165904
0.7576	Intermediate Similarity	NPC473204
0.7558	Intermediate Similarity	NPC476346
0.7556	Intermediate Similarity	NPC469806
0.7556	Intermediate Similarity	NPC469799
0.7556	Intermediate Similarity	NPC324170
0.7556	Intermediate Similarity	NPC469804
0.7556	Intermediate Similarity	NPC471218
0.7556	Intermediate Similarity	NPC471296
0.7556	Intermediate Similarity	NPC469805
0.7553	Intermediate Similarity	NPC118011
0.7553	Intermediate Similarity	NPC173042
0.7553	Intermediate Similarity	NPC73995
0.7553	Intermediate Similarity	NPC36668
0.7553	Intermediate Similarity	NPC470734
0.7551	Intermediate Similarity	NPC84335
0.7551	Intermediate Similarity	NPC475709
0.7551	Intermediate Similarity	NPC38530
0.7551	Intermediate Similarity	NPC476768
0.7551	Intermediate Similarity	NPC472188
0.7549	Intermediate Similarity	NPC252296
0.7529	Intermediate Similarity	NPC130016
0.7529	Intermediate Similarity	NPC109576
0.7529	Intermediate Similarity	NPC180015
0.7529	Intermediate Similarity	NPC56747
0.7529	Intermediate Similarity	NPC476490
0.7529	Intermediate Similarity	NPC476489
0.7528	Intermediate Similarity	NPC469798
0.7528	Intermediate Similarity	NPC469797
0.7528	Intermediate Similarity	NPC268827
0.7528	Intermediate Similarity	NPC195424
0.7527	Intermediate Similarity	NPC477228
0.7527	Intermediate Similarity	NPC312561
0.75	Intermediate Similarity	NPC472643
0.75	Intermediate Similarity	NPC472303
0.75	Intermediate Similarity	NPC65661
0.75	Intermediate Similarity	NPC42586
0.75	Intermediate Similarity	NPC473251
0.75	Intermediate Similarity	NPC300985
0.75	Intermediate Similarity	NPC63249
0.75	Intermediate Similarity	NPC217394
0.7476	Intermediate Similarity	NPC184512
0.7475	Intermediate Similarity	NPC476800
0.7475	Intermediate Similarity	NPC471366
0.7475	Intermediate Similarity	NPC318917
0.7475	Intermediate Similarity	NPC472186
0.7474	Intermediate Similarity	NPC8062
0.7474	Intermediate Similarity	NPC51486
0.7473	Intermediate Similarity	NPC3856
0.7473	Intermediate Similarity	NPC279639
0.7471	Intermediate Similarity	NPC40353
0.7451	Intermediate Similarity	NPC476764
0.7451	Intermediate Similarity	NPC476763
0.7449	Intermediate Similarity	NPC470801
0.7444	Intermediate Similarity	NPC475833
0.7426	Intermediate Similarity	NPC114540
0.7426	Intermediate Similarity	NPC32577
0.7426	Intermediate Similarity	NPC155332
0.7423	Intermediate Similarity	NPC470697
0.7423	Intermediate Similarity	NPC298973
0.7423	Intermediate Similarity	NPC475572
0.7423	Intermediate Similarity	NPC104925
0.7423	Intermediate Similarity	NPC84893
0.7423	Intermediate Similarity	NPC474555
0.7416	Intermediate Similarity	NPC190211
0.7416	Intermediate Similarity	NPC150646
0.7412	Intermediate Similarity	NPC181587
0.74	Intermediate Similarity	NPC473545
0.74	Intermediate Similarity	NPC470761
0.74	Intermediate Similarity	NPC54705
0.74	Intermediate Similarity	NPC473219
0.74	Intermediate Similarity	NPC472644
0.74	Intermediate Similarity	NPC472187
0.7396	Intermediate Similarity	NPC289479
0.7391	Intermediate Similarity	NPC474359
0.7391	Intermediate Similarity	NPC31086
0.7379	Intermediate Similarity	NPC476762
0.7379	Intermediate Similarity	NPC476761
0.7379	Intermediate Similarity	NPC476760
0.7374	Intermediate Similarity	NPC202705
0.7374	Intermediate Similarity	NPC2049
0.7374	Intermediate Similarity	NPC98112
0.7374	Intermediate Similarity	NPC476253
0.7368	Intermediate Similarity	NPC168131
0.7368	Intermediate Similarity	NPC293044
0.7368	Intermediate Similarity	NPC471654
0.7368	Intermediate Similarity	NPC174342
0.7368	Intermediate Similarity	NPC177141
0.7368	Intermediate Similarity	NPC174765
0.7363	Intermediate Similarity	NPC186276
0.7353	Intermediate Similarity	NPC134270
0.7347	Intermediate Similarity	NPC171395
0.7347	Intermediate Similarity	NPC471362
0.7347	Intermediate Similarity	NPC33473
0.7347	Intermediate Similarity	NPC471372
0.7347	Intermediate Similarity	NPC472189
0.7333	Intermediate Similarity	NPC473685
0.7333	Intermediate Similarity	NPC112457
0.7333	Intermediate Similarity	NPC137911
0.7333	Intermediate Similarity	NPC228477
0.7327	Intermediate Similarity	NPC168319
0.7327	Intermediate Similarity	NPC194028
0.7327	Intermediate Similarity	NPC310981
0.732	Intermediate Similarity	NPC115021
0.732	Intermediate Similarity	NPC476598
0.732	Intermediate Similarity	NPC476597
0.732	Intermediate Similarity	NPC1108
0.7317	Intermediate Similarity	NPC133904

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 NPC196407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1361
0.2-0.3	4082
0.3-0.4	2442
0.4-0.5	702
0.5-0.6	308
0.6-0.7	74
0.7-0.8	3
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
0.7753	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1694	Approved
0.7241	Intermediate Similarity	NPD4687	Approved
0.7241	Intermediate Similarity	NPD4058	Approved
0.7204	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8039	Approved
0.7083	Intermediate Similarity	NPD5737	Approved
0.7083	Intermediate Similarity	NPD6672	Approved
0.7075	Intermediate Similarity	NPD6686	Approved
0.7053	Intermediate Similarity	NPD7146	Approved
0.7053	Intermediate Similarity	NPD6684	Approved
0.7053	Intermediate Similarity	NPD5330	Approved
0.7053	Intermediate Similarity	NPD6409	Approved
0.7053	Intermediate Similarity	NPD7521	Approved
0.7053	Intermediate Similarity	NPD7334	Approved
0.7045	Intermediate Similarity	NPD5733	Approved
0.7041	Intermediate Similarity	NPD5694	Approved
0.7041	Intermediate Similarity	NPD5693	Phase 1
0.7011	Intermediate Similarity	NPD5276	Approved
0.6989	Remote Similarity	NPD5209	Approved
0.6988	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4137	Phase 3
0.6939	Remote Similarity	NPD5692	Phase 3
0.6939	Remote Similarity	NPD5207	Approved
0.6907	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6903	Approved
0.6897	Remote Similarity	NPD4691	Approved
0.6897	Remote Similarity	NPD4747	Approved
0.6869	Remote Similarity	NPD6050	Approved
0.67	Remote Similarity	NPD5284	Approved
0.67	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD3573	Approved
0.6569	Remote Similarity	NPD7748	Approved
0.6569	Remote Similarity	NPD7900	Approved
0.6569	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5208	Approved
0.6562	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD6412	Phase 2
0.6505	Remote Similarity	NPD5654	Approved
0.6505	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7638	Approved
0.6476	Remote Similarity	NPD5696	Approved
0.6436	Remote Similarity	NPD5785	Approved
0.6435	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.6381	Remote Similarity	NPD7902	Approved
0.6381	Remote Similarity	NPD5959	Approved
0.6373	Remote Similarity	NPD6411	Approved
0.6373	Remote Similarity	NPD7515	Phase 2
0.6373	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD5279	Phase 3
0.6364	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD6098	Approved
0.6364	Remote Similarity	NPD4623	Approved
0.6353	Remote Similarity	NPD4194	Approved
0.6353	Remote Similarity	NPD4193	Approved
0.6353	Remote Similarity	NPD4192	Approved
0.6353	Remote Similarity	NPD4191	Approved
0.6337	Remote Similarity	NPD6051	Approved
0.6327	Remote Similarity	NPD3665	Phase 1
0.6327	Remote Similarity	NPD3668	Phase 3
0.6327	Remote Similarity	NPD3133	Approved
0.6327	Remote Similarity	NPD3666	Approved
0.6321	Remote Similarity	NPD4225	Approved
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD5779	Approved
0.6289	Remote Similarity	NPD3667	Approved
0.6281	Remote Similarity	NPD7507	Approved
0.6273	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4695	Discontinued
0.625	Remote Similarity	NPD6001	Approved
0.6218	Remote Similarity	NPD7503	Approved
0.6216	Remote Similarity	NPD5697	Approved
0.6216	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3618	Phase 1
0.62	Remote Similarity	NPD4694	Approved
0.62	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.619	Remote Similarity	NPD287	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6176	Remote Similarity	NPD6101	Approved
0.6176	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4786	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6129	Remote Similarity	NPD7319	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6122	Remote Similarity	NPD4223	Phase 3
0.6122	Remote Similarity	NPD4221	Approved
0.6106	Remote Similarity	NPD6012	Approved
0.6106	Remote Similarity	NPD6013	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6014	Approved
0.6083	Remote Similarity	NPD8513	Phase 3
0.6083	Remote Similarity	NPD8515	Approved
0.6083	Remote Similarity	NPD8516	Approved
0.6083	Remote Similarity	NPD8517	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6058	Remote Similarity	NPD6079	Approved
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD5690	Phase 2
0.6038	Remote Similarity	NPD4629	Approved
0.6038	Remote Similarity	NPD5210	Approved
0.6034	Remote Similarity	NPD6858	Approved
0.6034	Remote Similarity	NPD7094	Approved
0.6019	Remote Similarity	NPD5328	Approved
0.6018	Remote Similarity	NPD7320	Approved
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD4197	Approved
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7732	Phase 3
0.5981	Remote Similarity	NPD5222	Approved
0.5966	Remote Similarity	NPD7328	Approved
0.5966	Remote Similarity	NPD7327	Approved
0.5965	Remote Similarity	NPD6373	Approved
0.5965	Remote Similarity	NPD6372	Approved
0.5963	Remote Similarity	NPD6404	Discontinued
0.5962	Remote Similarity	NPD6698	Approved
0.5962	Remote Similarity	NPD46	Approved
0.5955	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.595	Remote Similarity	NPD8033	Approved
0.5948	Remote Similarity	NPD6053	Discontinued
0.5948	Remote Similarity	NPD8297	Approved
0.5946	Remote Similarity	NPD6052	Approved
0.5941	Remote Similarity	NPD1696	Phase 3
0.5941	Remote Similarity	NPD5329	Approved
0.5941	Remote Similarity	NPD5363	Approved
0.5938	Remote Similarity	NPD4756	Discovery
0.5938	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6614	Approved
0.5926	Remote Similarity	NPD5173	Approved
0.5922	Remote Similarity	NPD4518	Approved
0.592	Remote Similarity	NPD7736	Approved
0.5917	Remote Similarity	NPD7516	Approved
0.5906	Remote Similarity	NPD7260	Phase 2
0.5902	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6370	Approved
0.59	Remote Similarity	NPD7154	Phase 3
0.59	Remote Similarity	NPD5362	Discontinued
0.5882	Remote Similarity	NPD5205	Approved
0.5882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4688	Approved
0.5882	Remote Similarity	NPD4689	Approved
0.5882	Remote Similarity	NPD4690	Approved
0.5882	Remote Similarity	NPD4693	Phase 3
0.5882	Remote Similarity	NPD4138	Approved
0.5876	Remote Similarity	NPD3617	Approved
0.5868	Remote Similarity	NPD8377	Approved
0.5868	Remote Similarity	NPD8294	Approved
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8028	Phase 2
0.5856	Remote Similarity	NPD5211	Phase 2
0.5856	Remote Similarity	NPD7632	Discontinued
0.5854	Remote Similarity	NPD8328	Phase 3
0.5849	Remote Similarity	NPD4202	Approved
0.584	Remote Similarity	NPD8293	Discontinued
0.5833	Remote Similarity	NPD4697	Phase 3
0.5833	Remote Similarity	NPD7839	Suspended
0.5827	Remote Similarity	NPD6914	Discontinued
0.5826	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.582	Remote Similarity	NPD8380	Approved
0.582	Remote Similarity	NPD8378	Approved
0.582	Remote Similarity	NPD8335	Approved
0.582	Remote Similarity	NPD8379	Approved
0.582	Remote Similarity	NPD8296	Approved
0.5818	Remote Similarity	NPD5285	Approved
0.5818	Remote Similarity	NPD5286	Approved
0.5818	Remote Similarity	NPD4696	Approved
0.581	Remote Similarity	NPD4096	Approved
0.5806	Remote Similarity	NPD7492	Approved
0.58	Remote Similarity	NPD4269	Approved
0.58	Remote Similarity	NPD4270	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