NPASS Compound

Structure

NPC268122 OpenBabel07101719132D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 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 0.8660 -0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 3.6808 -2.7024 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 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0875 -3.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	4.607
LogD:	4.152
LogS:	-4.549
# Rotatable Bonds:	2
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	4.465
Fsp3:	0.55
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:	-5.139
MDCK Permeability:	2.3120894184103236e-05
Pgp-inhibitor:	0.717
Pgp-substrate:	0.378
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.338

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.433
Plasma Protein Binding (PPB):	96.13955688476562%
Volume Distribution (VD):	1.987
Pgp-substrate:	3.6275227069854736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.168
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.324
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.509
CYP2C9-substrate:	0.59
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.642
CYP3A4-inhibitor:	0.269
CYP3A4-substrate:	0.397

ADMET: Excretion

Clearance (CL):	15.311
Half-life (T1/2):	0.587

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.153
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.569
Skin Sensitization:	0.513
Carcinogencity:	0.55
Eye Corrosion:	0.253
Eye Irritation:	0.228
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC268122

Natural Product ID:	NPC268122
*Common Name:**	6-Oxo-7,11,13-Labdatrien-16,15-Olide
IUPAC Name:	3-[(E)-2-[(1S,4aS,8aR)-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	FFMBCNCKQXNLJE-MMZWZMGNSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-13-10-16(21)18-19(2,3)8-5-9-20(18,4)15(13)7-6-14-11-17(22)23-12-14/h6-7,10-11,15,18H,5,8-9,12H2,1-4H3/b7-6+/t15-,18-,20+/m0/s1
SMILES:	CC1=CC(=O)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1/C=C/C1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506906
PubChem CID:	44574392
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	=	35.1	%	PMID[456042]

☑ 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 NPC268122 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	177
0.1-0.2	1203
0.2-0.3	5159
0.3-0.4	14187
0.4-0.5	10854
0.5-0.6	7354
0.6-0.7	3219
0.7-0.8	496
0.8-0.85	33
0.85-0.9	10
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.987	High Similarity	NPC118423
0.95	High Similarity	NPC168248
0.9487	High Similarity	NPC94200
0.9268	High Similarity	NPC196407
0.8837	High Similarity	NPC242069
0.8837	High Similarity	NPC469939
0.8831	High Similarity	NPC65650
0.8718	High Similarity	NPC4509
0.8706	High Similarity	NPC474844
0.8706	High Similarity	NPC284561
0.8675	High Similarity	NPC189311
0.8659	High Similarity	NPC474976
0.8659	High Similarity	NPC193198
0.8659	High Similarity	NPC474790
0.8636	High Similarity	NPC295347
0.8462	Intermediate Similarity	NPC20025
0.8444	Intermediate Similarity	NPC208094
0.8391	Intermediate Similarity	NPC220454
0.8391	Intermediate Similarity	NPC212679
0.8391	Intermediate Similarity	NPC469595
0.8372	Intermediate Similarity	NPC472302
0.8353	Intermediate Similarity	NPC220478
0.8333	Intermediate Similarity	NPC276336
0.8315	Intermediate Similarity	NPC477129
0.8315	Intermediate Similarity	NPC38830
0.8315	Intermediate Similarity	NPC477130
0.8313	Intermediate Similarity	NPC16321
0.8276	Intermediate Similarity	NPC5509
0.8272	Intermediate Similarity	NPC471220
0.8256	Intermediate Similarity	NPC163016
0.8256	Intermediate Similarity	NPC75315
0.825	Intermediate Similarity	NPC27205
0.8222	Intermediate Similarity	NPC209355
0.8214	Intermediate Similarity	NPC22611
0.8193	Intermediate Similarity	NPC282293
0.8182	Intermediate Similarity	NPC469372
0.8171	Intermediate Similarity	NPC471299
0.8161	Intermediate Similarity	NPC215831
0.8161	Intermediate Similarity	NPC226863
0.8148	Intermediate Similarity	NPC316500
0.8125	Intermediate Similarity	NPC476346
0.8118	Intermediate Similarity	NPC30486
0.8118	Intermediate Similarity	NPC470800
0.8118	Intermediate Similarity	NPC149869
0.8118	Intermediate Similarity	NPC475100
0.8101	Intermediate Similarity	NPC180015
0.8101	Intermediate Similarity	NPC130016
0.8101	Intermediate Similarity	NPC56747
0.8101	Intermediate Similarity	NPC109576
0.8095	Intermediate Similarity	NPC200513
0.8072	Intermediate Similarity	NPC268827
0.8072	Intermediate Similarity	NPC195424
0.8068	Intermediate Similarity	NPC173042
0.8068	Intermediate Similarity	NPC73995
0.8046	Intermediate Similarity	NPC181327
0.8046	Intermediate Similarity	NPC312561
0.8043	Intermediate Similarity	NPC110937
0.8025	Intermediate Similarity	NPC40353
0.8	Intermediate Similarity	NPC475657
0.7978	Intermediate Similarity	NPC8062
0.7975	Intermediate Similarity	NPC181587
0.7955	Intermediate Similarity	NPC477128
0.7952	Intermediate Similarity	NPC190211
0.7952	Intermediate Similarity	NPC150646
0.7935	Intermediate Similarity	NPC112654
0.7931	Intermediate Similarity	NPC472863
0.7895	Intermediate Similarity	NPC133904
0.7882	Intermediate Similarity	NPC186276
0.7882	Intermediate Similarity	NPC469804
0.7882	Intermediate Similarity	NPC471218
0.7882	Intermediate Similarity	NPC469799
0.7882	Intermediate Similarity	NPC469806
0.7882	Intermediate Similarity	NPC469805
0.7865	Intermediate Similarity	NPC118011
0.7865	Intermediate Similarity	NPC36668
0.7857	Intermediate Similarity	NPC469798
0.7857	Intermediate Similarity	NPC469797
0.7849	Intermediate Similarity	NPC84335
0.7849	Intermediate Similarity	NPC38530
0.7841	Intermediate Similarity	NPC477228
0.7831	Intermediate Similarity	NPC470052
0.7831	Intermediate Similarity	NPC105197
0.7816	Intermediate Similarity	NPC177932
0.7816	Intermediate Similarity	NPC86316
0.7816	Intermediate Similarity	NPC106416
0.7816	Intermediate Similarity	NPC329630
0.7816	Intermediate Similarity	NPC65661
0.7805	Intermediate Similarity	NPC469796
0.7805	Intermediate Similarity	NPC469793
0.7805	Intermediate Similarity	NPC19907
0.7802	Intermediate Similarity	NPC115021
0.7791	Intermediate Similarity	NPC3856
0.7791	Intermediate Similarity	NPC279639
0.7778	Intermediate Similarity	NPC152467
0.7778	Intermediate Similarity	NPC281942
0.7778	Intermediate Similarity	NPC232426
0.7778	Intermediate Similarity	NPC51486
0.7765	Intermediate Similarity	NPC474955
0.7765	Intermediate Similarity	NPC475833
0.7753	Intermediate Similarity	NPC24816
0.775	Intermediate Similarity	NPC133253
0.775	Intermediate Similarity	NPC257618
0.7717	Intermediate Similarity	NPC470697
0.7717	Intermediate Similarity	NPC84893
0.7711	Intermediate Similarity	NPC472300
0.7711	Intermediate Similarity	NPC54996
0.7708	Intermediate Similarity	NPC114540
0.7708	Intermediate Similarity	NPC155332
0.7708	Intermediate Similarity	NPC32577
0.7701	Intermediate Similarity	NPC71626
0.7701	Intermediate Similarity	NPC31086
0.7701	Intermediate Similarity	NPC87552
0.7701	Intermediate Similarity	NPC474359
0.7692	Intermediate Similarity	NPC65513
0.7692	Intermediate Similarity	NPC303697
0.7692	Intermediate Similarity	NPC141831
0.7684	Intermediate Similarity	NPC477720
0.7684	Intermediate Similarity	NPC54705
0.7683	Intermediate Similarity	NPC473171
0.7683	Intermediate Similarity	NPC228978
0.7674	Intermediate Similarity	NPC178676
0.7667	Intermediate Similarity	NPC168131
0.7667	Intermediate Similarity	NPC471654
0.7667	Intermediate Similarity	NPC174342
0.7667	Intermediate Similarity	NPC177141
0.766	Intermediate Similarity	NPC202705
0.766	Intermediate Similarity	NPC2049
0.7634	Intermediate Similarity	NPC33473
0.7634	Intermediate Similarity	NPC171395
0.7629	Intermediate Similarity	NPC132395
0.7629	Intermediate Similarity	NPC471365
0.7629	Intermediate Similarity	NPC471364
0.7619	Intermediate Similarity	NPC4827
0.7619	Intermediate Similarity	NPC184737
0.7614	Intermediate Similarity	NPC110405
0.7614	Intermediate Similarity	NPC323765
0.7614	Intermediate Similarity	NPC470048
0.7609	Intermediate Similarity	NPC476598
0.7609	Intermediate Similarity	NPC476597
0.7609	Intermediate Similarity	NPC1108
0.7604	Intermediate Similarity	NPC310981
0.7604	Intermediate Similarity	NPC168319
0.7604	Intermediate Similarity	NPC194028
0.76	Intermediate Similarity	NPC228477
0.76	Intermediate Similarity	NPC137911
0.7595	Intermediate Similarity	NPC310992
0.7595	Intermediate Similarity	NPC188292
0.7595	Intermediate Similarity	NPC155198
0.7595	Intermediate Similarity	NPC260474
0.759	Intermediate Similarity	NPC473223
0.759	Intermediate Similarity	NPC474463
0.759	Intermediate Similarity	NPC41017
0.7586	Intermediate Similarity	NPC42476
0.7582	Intermediate Similarity	NPC310479
0.7582	Intermediate Similarity	NPC182136
0.7582	Intermediate Similarity	NPC475965
0.7582	Intermediate Similarity	NPC471818
0.7582	Intermediate Similarity	NPC221111
0.7582	Intermediate Similarity	NPC273199
0.7582	Intermediate Similarity	NPC474842
0.7582	Intermediate Similarity	NPC280149
0.7579	Intermediate Similarity	NPC108368
0.7579	Intermediate Similarity	NPC57079
0.7564	Intermediate Similarity	NPC185587
0.7561	Intermediate Similarity	NPC474796
0.7561	Intermediate Similarity	NPC329866
0.7561	Intermediate Similarity	NPC474797
0.7558	Intermediate Similarity	NPC42470
0.7558	Intermediate Similarity	NPC475665
0.7556	Intermediate Similarity	NPC97884
0.7556	Intermediate Similarity	NPC472220
0.7553	Intermediate Similarity	NPC311166
0.7551	Intermediate Similarity	NPC189616
0.7532	Intermediate Similarity	NPC226066
0.7532	Intermediate Similarity	NPC329698
0.7531	Intermediate Similarity	NPC54123
0.7531	Intermediate Similarity	NPC21944
0.7529	Intermediate Similarity	NPC170793
0.7528	Intermediate Similarity	NPC471219
0.7528	Intermediate Similarity	NPC195640
0.7527	Intermediate Similarity	NPC56525
0.7527	Intermediate Similarity	NPC476596
0.7527	Intermediate Similarity	NPC53685
0.7526	Intermediate Similarity	NPC31058
0.7526	Intermediate Similarity	NPC273005
0.7526	Intermediate Similarity	NPC469606
0.75	Intermediate Similarity	NPC473825
0.75	Intermediate Similarity	NPC472814
0.75	Intermediate Similarity	NPC256846
0.75	Intermediate Similarity	NPC266955
0.75	Intermediate Similarity	NPC166110
0.75	Intermediate Similarity	NPC49420
0.75	Intermediate Similarity	NPC177037
0.75	Intermediate Similarity	NPC187568
0.75	Intermediate Similarity	NPC139566
0.75	Intermediate Similarity	NPC41780
0.75	Intermediate Similarity	NPC476299
0.75	Intermediate Similarity	NPC220155
0.75	Intermediate Similarity	NPC473986
0.75	Intermediate Similarity	NPC470557

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 NPC268122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1283
0.2-0.3	3983
0.3-0.4	2561
0.4-0.5	749
0.5-0.6	304
0.6-0.7	94
0.7-0.8	15
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
0.8095	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD1694	Approved
0.7778	Intermediate Similarity	NPD4058	Approved
0.7778	Intermediate Similarity	NPD4687	Approved
0.7683	Intermediate Similarity	NPD8039	Approved
0.7561	Intermediate Similarity	NPD5733	Approved
0.7532	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5276	Approved
0.7528	Intermediate Similarity	NPD7334	Approved
0.7528	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD7521	Approved
0.7528	Intermediate Similarity	NPD7146	Approved
0.7528	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD4137	Phase 3
0.7407	Intermediate Similarity	NPD4747	Approved
0.7407	Intermediate Similarity	NPD4691	Approved
0.7391	Intermediate Similarity	NPD5207	Approved
0.7363	Intermediate Similarity	NPD6672	Approved
0.7363	Intermediate Similarity	NPD5737	Approved
0.7363	Intermediate Similarity	NPD6903	Approved
0.7363	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5693	Phase 1
0.7312	Intermediate Similarity	NPD5694	Approved
0.7273	Intermediate Similarity	NPD5209	Approved
0.7204	Intermediate Similarity	NPD5692	Phase 3
0.7128	Intermediate Similarity	NPD6050	Approved
0.7065	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5208	Approved
0.6951	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5281	Approved
0.6947	Remote Similarity	NPD5284	Approved
0.6915	Remote Similarity	NPD6673	Approved
0.6915	Remote Similarity	NPD6904	Approved
0.6915	Remote Similarity	NPD6080	Approved
0.6907	Remote Similarity	NPD5695	Phase 3
0.6875	Remote Similarity	NPD6399	Phase 3
0.6835	Remote Similarity	NPD4191	Approved
0.6835	Remote Similarity	NPD4192	Approved
0.6835	Remote Similarity	NPD4193	Approved
0.6835	Remote Similarity	NPD4194	Approved
0.6804	Remote Similarity	NPD7900	Approved
0.6804	Remote Similarity	NPD7748	Approved
0.6804	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4519	Discontinued
0.6774	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD5279	Phase 3
0.6774	Remote Similarity	NPD6098	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6739	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3665	Phase 1
0.6739	Remote Similarity	NPD3666	Approved
0.6739	Remote Similarity	NPD3133	Approved
0.6737	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5654	Approved
0.6703	Remote Similarity	NPD3667	Approved
0.67	Remote Similarity	NPD7638	Approved
0.67	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD287	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6633	Remote Similarity	NPD6001	Approved
0.66	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD5959	Approved
0.6598	Remote Similarity	NPD6411	Approved
0.6598	Remote Similarity	NPD7637	Suspended
0.6598	Remote Similarity	NPD7515	Phase 2
0.6596	Remote Similarity	NPD3618	Phase 1
0.6596	Remote Similarity	NPD4694	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6562	Remote Similarity	NPD6051	Approved
0.6559	Remote Similarity	NPD3668	Phase 3
0.6559	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD4225	Approved
0.6531	Remote Similarity	NPD5778	Approved
0.6531	Remote Similarity	NPD5779	Approved
0.6522	Remote Similarity	NPD4221	Approved
0.6522	Remote Similarity	NPD4223	Phase 3
0.6509	Remote Similarity	NPD6686	Approved
0.6484	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4695	Discontinued
0.6476	Remote Similarity	NPD6008	Approved
0.6444	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6079	Approved
0.6421	Remote Similarity	NPD5690	Phase 2
0.6415	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6101	Approved
0.6392	Remote Similarity	NPD5328	Approved
0.6392	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4753	Phase 2
0.6386	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4197	Approved
0.6364	Remote Similarity	NPD7094	Approved
0.6364	Remote Similarity	NPD6858	Approved
0.6355	Remote Similarity	NPD6881	Approved
0.6355	Remote Similarity	NPD6899	Approved
0.6355	Remote Similarity	NPD6011	Approved
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD1696	Phase 3
0.6316	Remote Similarity	NPD5329	Approved
0.6311	Remote Similarity	NPD6404	Discontinued
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6014	Approved
0.6296	Remote Similarity	NPD6013	Approved
0.6296	Remote Similarity	NPD6012	Approved
0.6289	Remote Similarity	NPD4518	Approved
0.6264	Remote Similarity	NPD3617	Approved
0.6262	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD4138	Approved
0.625	Remote Similarity	NPD4688	Approved
0.625	Remote Similarity	NPD4689	Approved
0.625	Remote Similarity	NPD4690	Approved
0.625	Remote Similarity	NPD4693	Phase 3
0.625	Remote Similarity	NPD5205	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5210	Approved
0.6238	Remote Similarity	NPD4629	Approved
0.6237	Remote Similarity	NPD8028	Phase 2
0.6207	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7320	Approved
0.62	Remote Similarity	NPD4202	Approved
0.6182	Remote Similarity	NPD6649	Approved
0.6182	Remote Similarity	NPD6847	Approved
0.6182	Remote Similarity	NPD6869	Approved
0.6182	Remote Similarity	NPD8130	Phase 1
0.6182	Remote Similarity	NPD6650	Approved
0.6182	Remote Similarity	NPD6617	Approved
0.6176	Remote Similarity	NPD7732	Phase 3
0.6176	Remote Similarity	NPD5221	Approved
0.6176	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5222	Approved
0.6162	Remote Similarity	NPD6698	Approved
0.6162	Remote Similarity	NPD46	Approved
0.6162	Remote Similarity	NPD4096	Approved
0.6154	Remote Similarity	NPD4756	Discovery
0.6147	Remote Similarity	NPD6373	Approved
0.6147	Remote Similarity	NPD6372	Approved
0.6146	Remote Similarity	NPD5363	Approved
0.6132	Remote Similarity	NPD6052	Approved
0.6126	Remote Similarity	NPD6053	Discontinued
0.6126	Remote Similarity	NPD8297	Approved
0.6126	Remote Similarity	NPD6882	Approved
0.6117	Remote Similarity	NPD5173	Approved
0.6111	Remote Similarity	NPD6614	Approved
0.6111	Remote Similarity	NPD8264	Approved
0.6105	Remote Similarity	NPD5362	Discontinued
0.6105	Remote Similarity	NPD7154	Phase 3
0.6082	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7260	Phase 2
0.604	Remote Similarity	NPD5133	Approved
0.6038	Remote Similarity	NPD5211	Phase 2
0.6038	Remote Similarity	NPD7632	Discontinued
0.6036	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4195	Approved
0.6019	Remote Similarity	NPD4697	Phase 3
0.6017	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD4219	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5286	Approved
0.5979	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6868	Approved
0.5963	Remote Similarity	NPD6412	Phase 2
0.5962	Remote Similarity	NPD3495	Discontinued
0.5962	Remote Similarity	NPD4755	Approved
0.5957	Remote Similarity	NPD4252	Approved
0.5946	Remote Similarity	NPD2067	Discontinued
0.5943	Remote Similarity	NPD5223	Approved
0.5929	Remote Similarity	NPD4632	Approved
0.5926	Remote Similarity	NPD5141	Approved
0.5926	Remote Similarity	NPD5909	Discontinued
0.5918	Remote Similarity	NPD5786	Approved
0.5914	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6317	Approved
0.5905	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.59	Remote Similarity	NPD1695	Approved
0.5895	Remote Similarity	NPD5369	Approved
0.5888	Remote Similarity	NPD5225	Approved
0.5888	Remote Similarity	NPD5224	Approved
0.5888	Remote Similarity	NPD5226	Approved
0.5888	Remote Similarity	NPD4633	Approved
0.5882	Remote Similarity	NPD7631	Approved
0.5877	Remote Similarity	NPD6010	Discontinued
0.5865	Remote Similarity	NPD7614	Phase 1

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