NPASS Compound

Structure

NPC27205 OpenBabel07101719142D 28 29 0 0 0 0 0 0 0 0999 V2000 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4282 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9282 3.6728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1603 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6962 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1603 5.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0263 6.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 18 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 21 2 0 0 0 0 16 25 1 0 0 0 0 17 28 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 26 2 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.27
Volume:	434.395
LogP:	5.854
LogD:	4.882
LogS:	-4.862
# Rotatable Bonds:	8
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.494
Synthetic Accessibility Score:	4.104
Fsp3:	0.56
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:	-4.852
MDCK Permeability:	2.2891863409313373e-05
Pgp-inhibitor:	0.336
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.724
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	95.29299926757812%
Volume Distribution (VD):	2.322
Pgp-substrate:	0.7056710124015808%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.388
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.651
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.428
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	5.841
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.136
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.191
Carcinogencity:	0.224
Eye Corrosion:	0.008
Eye Irritation:	0.077
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC27205

Natural Product ID:	NPC27205
*Common Name:**	Isodehydroluffariellolide
IUPAC Name:	4-[(3E,7E)-4,8-dimethyl-10-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)deca-3,7-dienyl]-2H-furan-5-one
Synonyms:	Isodehydroluffariellolide
Standard InCHIKey:	PRRMUPFGQLWFJH-IWJUANJQSA-N
Standard InCHI:	InChI=1S/C25H36O3/c1-18(10-7-11-21-15-17-28-24(21)27)8-6-9-19(2)12-13-22-20(3)23(26)14-16-25(22,4)5/h9-10,15H,6-8,11-14,16-17H2,1-5H3/b18-10+,19-9+
SMILES:	C/C(=CCC/C(=C/CCC1=CCOC1=O)/C)/CCC1=C(C)C(=O)CCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498285
PubChem CID:	6450975
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
NPO32964	hyrtios cf. erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869210]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	Activity	=	45.0	%	PMID[456484]

☑ 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 NPC27205 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	180
0.1-0.2	1426
0.2-0.3	7216
0.3-0.4	16145
0.4-0.5	8760
0.5-0.6	5684
0.6-0.7	2835
0.7-0.8	402
0.8-0.85	39
0.85-0.9	6
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC257618
0.9324	High Similarity	NPC471299
0.9189	High Similarity	NPC471220
0.8734	High Similarity	NPC31086
0.8625	High Similarity	NPC474860
0.8625	High Similarity	NPC471300
0.8625	High Similarity	NPC189311
0.8608	High Similarity	NPC193198
0.8514	High Similarity	NPC222244
0.8514	High Similarity	NPC16349
0.85	High Similarity	NPC149869
0.85	High Similarity	NPC475100
0.8375	Intermediate Similarity	NPC118423
0.8333	Intermediate Similarity	NPC150646
0.8312	Intermediate Similarity	NPC187568
0.8312	Intermediate Similarity	NPC41780
0.8289	Intermediate Similarity	NPC228978
0.8289	Intermediate Similarity	NPC65650
0.8272	Intermediate Similarity	NPC474865
0.8267	Intermediate Similarity	NPC476489
0.8267	Intermediate Similarity	NPC476490
0.825	Intermediate Similarity	NPC268122
0.825	Intermediate Similarity	NPC471296
0.825	Intermediate Similarity	NPC94200
0.825	Intermediate Similarity	NPC200513
0.8214	Intermediate Similarity	NPC5509
0.8205	Intermediate Similarity	NPC128276
0.8182	Intermediate Similarity	NPC40353
0.8182	Intermediate Similarity	NPC473223
0.8158	Intermediate Similarity	NPC20025
0.8125	Intermediate Similarity	NPC471325
0.8118	Intermediate Similarity	NPC471818
0.8101	Intermediate Similarity	NPC469690
0.8095	Intermediate Similarity	NPC226863
0.8082	Intermediate Similarity	NPC203335
0.8077	Intermediate Similarity	NPC262747
0.8077	Intermediate Similarity	NPC57744
0.8072	Intermediate Similarity	NPC168248
0.8072	Intermediate Similarity	NPC220478
0.8049	Intermediate Similarity	NPC30486
0.8049	Intermediate Similarity	NPC474359
0.8046	Intermediate Similarity	NPC476596
0.8026	Intermediate Similarity	NPC276336
0.8	Intermediate Similarity	NPC469660
0.7976	Intermediate Similarity	NPC312561
0.7975	Intermediate Similarity	NPC209135
0.7975	Intermediate Similarity	NPC474816
0.7973	Intermediate Similarity	NPC218477
0.7952	Intermediate Similarity	NPC65661
0.7952	Intermediate Similarity	NPC86316
0.7952	Intermediate Similarity	NPC106416
0.7931	Intermediate Similarity	NPC476598
0.7931	Intermediate Similarity	NPC476597
0.7927	Intermediate Similarity	NPC22611
0.7922	Intermediate Similarity	NPC294434
0.7922	Intermediate Similarity	NPC259599
0.7922	Intermediate Similarity	NPC15499
0.7922	Intermediate Similarity	NPC117746
0.7922	Intermediate Similarity	NPC474758
0.7907	Intermediate Similarity	NPC51486
0.7901	Intermediate Similarity	NPC282293
0.7895	Intermediate Similarity	NPC84038
0.7875	Intermediate Similarity	NPC469620
0.7875	Intermediate Similarity	NPC178277
0.7857	Intermediate Similarity	NPC472863
0.7848	Intermediate Similarity	NPC316500
0.7848	Intermediate Similarity	NPC473756
0.7838	Intermediate Similarity	NPC472266
0.7821	Intermediate Similarity	NPC244166
0.7816	Intermediate Similarity	NPC473944
0.7808	Intermediate Similarity	NPC470688
0.7805	Intermediate Similarity	NPC173609
0.7805	Intermediate Similarity	NPC178676
0.7792	Intermediate Similarity	NPC474705
0.7791	Intermediate Similarity	NPC284561
0.7791	Intermediate Similarity	NPC174342
0.775	Intermediate Similarity	NPC299235
0.7746	Intermediate Similarity	NPC79756
0.7738	Intermediate Similarity	NPC177932
0.7738	Intermediate Similarity	NPC110405
0.7733	Intermediate Similarity	NPC276290
0.7733	Intermediate Similarity	NPC470256
0.7727	Intermediate Similarity	NPC115021
0.7727	Intermediate Similarity	NPC475657
0.7722	Intermediate Similarity	NPC123360
0.7711	Intermediate Similarity	NPC475947
0.7711	Intermediate Similarity	NPC474193
0.7711	Intermediate Similarity	NPC474976
0.7711	Intermediate Similarity	NPC12283
0.7711	Intermediate Similarity	NPC474790
0.7701	Intermediate Similarity	NPC8062
0.7701	Intermediate Similarity	NPC281942
0.7701	Intermediate Similarity	NPC232426
0.7692	Intermediate Similarity	NPC476355
0.7692	Intermediate Similarity	NPC140287
0.7683	Intermediate Similarity	NPC475944
0.7683	Intermediate Similarity	NPC275507
0.7683	Intermediate Similarity	NPC42470
0.7674	Intermediate Similarity	NPC472302
0.7674	Intermediate Similarity	NPC196407
0.7674	Intermediate Similarity	NPC215831
0.7671	Intermediate Similarity	NPC226066
0.7671	Intermediate Similarity	NPC34883
0.7662	Intermediate Similarity	NPC186531
0.7662	Intermediate Similarity	NPC163003
0.7647	Intermediate Similarity	NPC474045
0.7647	Intermediate Similarity	NPC261253
0.764	Intermediate Similarity	NPC148463
0.764	Intermediate Similarity	NPC476415
0.7639	Intermediate Similarity	NPC151648
0.7632	Intermediate Similarity	NPC265574
0.7625	Intermediate Similarity	NPC65603
0.7614	Intermediate Similarity	NPC472705
0.7614	Intermediate Similarity	NPC472814
0.7614	Intermediate Similarity	NPC141831
0.7614	Intermediate Similarity	NPC177037
0.7595	Intermediate Similarity	NPC329852
0.7595	Intermediate Similarity	NPC155587
0.7595	Intermediate Similarity	NPC469414
0.7595	Intermediate Similarity	NPC138408
0.7595	Intermediate Similarity	NPC226669
0.7595	Intermediate Similarity	NPC193351
0.7595	Intermediate Similarity	NPC329826
0.759	Intermediate Similarity	NPC471298
0.759	Intermediate Similarity	NPC186276
0.759	Intermediate Similarity	NPC323251
0.759	Intermediate Similarity	NPC35556
0.759	Intermediate Similarity	NPC471218
0.7586	Intermediate Similarity	NPC73995
0.7586	Intermediate Similarity	NPC251528
0.7586	Intermediate Similarity	NPC474844
0.7582	Intermediate Similarity	NPC53844
0.7568	Intermediate Similarity	NPC133904
0.7561	Intermediate Similarity	NPC47747
0.7561	Intermediate Similarity	NPC268827
0.7561	Intermediate Similarity	NPC195424
0.7558	Intermediate Similarity	NPC475678
0.7558	Intermediate Similarity	NPC478144
0.7558	Intermediate Similarity	NPC478145
0.7558	Intermediate Similarity	NPC477228
0.7556	Intermediate Similarity	NPC295347
0.7556	Intermediate Similarity	NPC209355
0.7534	Intermediate Similarity	NPC155849
0.7532	Intermediate Similarity	NPC67183
0.7531	Intermediate Similarity	NPC184737
0.7531	Intermediate Similarity	NPC253749
0.7529	Intermediate Similarity	NPC155873
0.7528	Intermediate Similarity	NPC139692
0.7528	Intermediate Similarity	NPC469939
0.75	Intermediate Similarity	NPC212679
0.75	Intermediate Similarity	NPC152467
0.75	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC235906
0.75	Intermediate Similarity	NPC476369
0.75	Intermediate Similarity	NPC101651
0.75	Intermediate Similarity	NPC222358
0.75	Intermediate Similarity	NPC4509
0.75	Intermediate Similarity	NPC471297
0.75	Intermediate Similarity	NPC476437
0.75	Intermediate Similarity	NPC474809
0.75	Intermediate Similarity	NPC469595
0.75	Intermediate Similarity	NPC220454
0.75	Intermediate Similarity	NPC159748
0.7473	Intermediate Similarity	NPC29952
0.747	Intermediate Similarity	NPC40228
0.747	Intermediate Similarity	NPC14203
0.747	Intermediate Similarity	NPC229584
0.747	Intermediate Similarity	NPC325031
0.747	Intermediate Similarity	NPC281949
0.747	Intermediate Similarity	NPC301477
0.747	Intermediate Similarity	NPC25684
0.747	Intermediate Similarity	NPC475665
0.7467	Intermediate Similarity	NPC248125
0.7444	Intermediate Similarity	NPC477130
0.7444	Intermediate Similarity	NPC477129
0.7444	Intermediate Similarity	NPC470697
0.7444	Intermediate Similarity	NPC84893
0.7444	Intermediate Similarity	NPC53685
0.7442	Intermediate Similarity	NPC316426
0.7442	Intermediate Similarity	NPC195640
0.7442	Intermediate Similarity	NPC469483
0.7442	Intermediate Similarity	NPC261721
0.7442	Intermediate Similarity	NPC211892
0.7442	Intermediate Similarity	NPC315395
0.7439	Intermediate Similarity	NPC63649
0.7439	Intermediate Similarity	NPC270126
0.7439	Intermediate Similarity	NPC190211
0.7439	Intermediate Similarity	NPC472965
0.7439	Intermediate Similarity	NPC264227
0.7432	Intermediate Similarity	NPC329698
0.7419	Intermediate Similarity	NPC54705
0.7416	Intermediate Similarity	NPC477783
0.7416	Intermediate Similarity	NPC221282
0.7416	Intermediate Similarity	NPC65513
0.7412	Intermediate Similarity	NPC163615
0.7412	Intermediate Similarity	NPC238197
0.7412	Intermediate Similarity	NPC38569
0.7412	Intermediate Similarity	NPC126518
0.7412	Intermediate Similarity	NPC471301
0.7412	Intermediate Similarity	NPC71626

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 NPC27205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1932
0.2-0.3	4192
0.3-0.4	1971
0.4-0.5	586
0.5-0.6	238
0.6-0.7	57
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8289	Intermediate Similarity	NPD8039	Approved
0.825	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1694	Approved
0.7671	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7334	Approved
0.7442	Intermediate Similarity	NPD7146	Approved
0.7442	Intermediate Similarity	NPD6684	Approved
0.7442	Intermediate Similarity	NPD7521	Approved
0.7442	Intermediate Similarity	NPD6409	Approved
0.7442	Intermediate Similarity	NPD5330	Approved
0.7412	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5209	Approved
0.7333	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6672	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5737	Approved
0.7273	Intermediate Similarity	NPD6903	Approved
0.7111	Intermediate Similarity	NPD5785	Approved
0.7033	Intermediate Similarity	NPD5693	Phase 1
0.6905	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4691	Approved
0.6813	Remote Similarity	NPD6904	Approved
0.6813	Remote Similarity	NPD6673	Approved
0.6813	Remote Similarity	NPD6080	Approved
0.6795	Remote Similarity	NPD7331	Phase 2
0.6778	Remote Similarity	NPD3573	Approved
0.675	Remote Similarity	NPD4137	Phase 3
0.6739	Remote Similarity	NPD6698	Approved
0.6739	Remote Similarity	NPD46	Approved
0.6733	Remote Similarity	NPD6686	Approved
0.6714	Remote Similarity	NPD6927	Phase 3
0.6711	Remote Similarity	NPD4194	Approved
0.6711	Remote Similarity	NPD4192	Approved
0.6711	Remote Similarity	NPD4191	Approved
0.6711	Remote Similarity	NPD4193	Approved
0.6703	Remote Similarity	NPD5208	Approved
0.6702	Remote Similarity	NPD7900	Approved
0.6702	Remote Similarity	NPD7748	Approved
0.6702	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6098	Approved
0.6632	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5695	Phase 3
0.6627	Remote Similarity	NPD4058	Approved
0.6627	Remote Similarity	NPD5733	Approved
0.6598	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD6399	Phase 3
0.6588	Remote Similarity	NPD4756	Discovery
0.6585	Remote Similarity	NPD5276	Approved
0.6582	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5207	Approved
0.6559	Remote Similarity	NPD5692	Phase 3
0.6556	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5363	Approved
0.6552	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7640	Approved
0.6531	Remote Similarity	NPD7639	Approved
0.6517	Remote Similarity	NPD7154	Phase 3
0.6495	Remote Similarity	NPD7902	Approved
0.6489	Remote Similarity	NPD7515	Phase 2
0.6489	Remote Similarity	NPD5694	Approved
0.6452	Remote Similarity	NPD6051	Approved
0.6444	Remote Similarity	NPD3666	Approved
0.6444	Remote Similarity	NPD3133	Approved
0.6444	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD4687	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6389	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD4695	Discontinued
0.6354	Remote Similarity	NPD6001	Approved
0.6333	Remote Similarity	NPD5362	Discontinued
0.6316	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD287	Approved
0.6304	Remote Similarity	NPD4519	Discontinued
0.6304	Remote Similarity	NPD3618	Phase 1
0.6304	Remote Similarity	NPD5279	Phase 3
0.6304	Remote Similarity	NPD4623	Approved
0.6286	Remote Similarity	NPD6371	Approved
0.6277	Remote Similarity	NPD5328	Approved
0.6277	Remote Similarity	NPD1695	Approved
0.6264	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD5778	Approved
0.6224	Remote Similarity	NPD7732	Phase 3
0.6222	Remote Similarity	NPD4269	Approved
0.6222	Remote Similarity	NPD4221	Approved
0.6222	Remote Similarity	NPD4223	Phase 3
0.6222	Remote Similarity	NPD6435	Approved
0.6222	Remote Similarity	NPD4270	Approved
0.6222	Remote Similarity	NPD3667	Approved
0.622	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6675	Approved
0.6214	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD5739	Approved
0.6214	Remote Similarity	NPD6402	Approved
0.6196	Remote Similarity	NPD1696	Phase 3
0.6196	Remote Similarity	NPD5329	Approved
0.6196	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4252	Approved
0.6154	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD5284	Approved
0.6146	Remote Similarity	NPD5281	Approved
0.6146	Remote Similarity	NPD7637	Suspended
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6129	Remote Similarity	NPD5786	Approved
0.6129	Remote Similarity	NPD5690	Phase 2
0.6122	Remote Similarity	NPD5654	Approved
0.6111	Remote Similarity	NPD5369	Approved
0.6105	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4753	Phase 2
0.6105	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6101	Approved
0.6095	Remote Similarity	NPD6011	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6087	Remote Similarity	NPD4197	Approved
0.6087	Remote Similarity	NPD3668	Phase 3
0.6075	Remote Similarity	NPD6650	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6075	Remote Similarity	NPD6649	Approved
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD6847	Approved
0.6075	Remote Similarity	NPD6617	Approved
0.6058	Remote Similarity	NPD6008	Approved
0.6056	Remote Similarity	NPD5343	Approved
0.6042	Remote Similarity	NPD7838	Discovery
0.604	Remote Similarity	NPD6404	Discontinued
0.6038	Remote Similarity	NPD6014	Approved
0.6038	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD6372	Approved
0.6038	Remote Similarity	NPD6013	Approved
0.6038	Remote Similarity	NPD6373	Approved
0.6027	Remote Similarity	NPD29	Approved
0.6027	Remote Similarity	NPD28	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6019	Remote Similarity	NPD6052	Approved
0.6019	Remote Similarity	NPD6053	Discontinued
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6614	Approved
0.5981	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4629	Approved
0.596	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5205	Approved
0.5957	Remote Similarity	NPD4689	Approved
0.5957	Remote Similarity	NPD4688	Approved
0.5957	Remote Similarity	NPD4690	Approved
0.5957	Remote Similarity	NPD4138	Approved
0.5957	Remote Similarity	NPD4693	Phase 3
0.5957	Remote Similarity	NPD5280	Approved
0.5957	Remote Similarity	NPD4694	Approved
0.5955	Remote Similarity	NPD3617	Approved
0.5941	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD8028	Phase 2
0.5926	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7632	Discontinued
0.5921	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4202	Approved
0.59	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5221	Approved
0.59	Remote Similarity	NPD5222	Approved
0.59	Remote Similarity	NPD7614	Phase 1
0.5859	Remote Similarity	NPD5282	Discontinued
0.5856	Remote Similarity	NPD6868	Approved
0.5849	Remote Similarity	NPD6412	Phase 2
0.5844	Remote Similarity	NPD4219	Approved
0.5842	Remote Similarity	NPD5173	Approved
0.5833	Remote Similarity	NPD4518	Approved
0.5833	Remote Similarity	NPD2067	Discontinued
0.5824	Remote Similarity	NPD4821	Approved
0.5824	Remote Similarity	NPD4819	Approved
0.5824	Remote Similarity	NPD4820	Approved
0.5824	Remote Similarity	NPD4822	Approved
0.5818	Remote Similarity	NPD7094	Approved
0.5818	Remote Similarity	NPD6858	Approved
0.5816	Remote Similarity	NPD7983	Approved
0.5806	Remote Similarity	NPD5332	Approved
0.5806	Remote Similarity	NPD4788	Approved
0.5806	Remote Similarity	NPD5331	Approved
0.5789	Remote Similarity	NPD3195	Phase 2

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