NPASS Compound

Structure

NPC71626 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 1.3685 1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6369 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6994 1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0084 2.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 1.7601 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 10 1 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 1 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 6 0 0 0 15 21 1 0 0 0 0 17 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	304.17
LogP:	4.212
LogD:	3.362
LogS:	-3.654
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.796
Synthetic Accessibility Score:	4.015
Fsp3:	0.706
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:	-4.712
MDCK Permeability:	2.6807481845025904e-05
Pgp-inhibitor:	0.092
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.358
Plasma Protein Binding (PPB):	92.40218353271484%
Volume Distribution (VD):	0.74
Pgp-substrate:	12.99565315246582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.262
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.495
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	5.759
Half-life (T1/2):	0.492

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.335
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.232
Skin Sensitization:	0.849
Carcinogencity:	0.865
Eye Corrosion:	0.024
Eye Irritation:	0.252
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC71626

Natural Product ID:	NPC71626
*Common Name:**	[(1R,5As,9As)-6,6,9A-Trimethyl-3-Oxo-4,5,5A,7,8,9-Hexahydro-1H-Benzo[G][2]Benzofuran-1-Yl] Acetate
IUPAC Name:	[(1R,5aS,9aS)-6,6,9a-trimethyl-3-oxo-4,5,5a,7,8,9-hexahydro-1H-benzo[g][2]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	YPCAJBFKJXGFFT-MJEQTWJJSA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-10(18)20-15-13-11(14(19)21-15)6-7-12-16(2,3)8-5-9-17(12,13)4/h12,15H,5-9H2,1-4H3/t12-,15+,17-/m0/s1
SMILES:	CC(=O)O[C@@H]1OC(=O)C2=C1[C@@]1(C)CCCC([C@@H]1CC2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456856
PubChem CID:	10613596
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO30670	Dysidea	Genus	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374954]
NPO30670	Dysidea	Genus	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21214221]
NPO30670	Dysidea	Genus	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392880]

☑ 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
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	98000.0	nM	PMID[516083]

☑ 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 NPC71626 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	210
0.1-0.2	1533
0.2-0.3	6230
0.3-0.4	14596
0.4-0.5	8996
0.5-0.6	7361
0.6-0.7	3240
0.7-0.8	480
0.8-0.85	31
0.85-0.9	15
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC316500
0.9036	High Similarity	NPC474062
0.8966	High Similarity	NPC474554
0.8953	High Similarity	NPC65513
0.8902	High Similarity	NPC472440
0.8764	High Similarity	NPC17578
0.8764	High Similarity	NPC240673
0.869	High Similarity	NPC189311
0.869	High Similarity	NPC472442
0.8659	High Similarity	NPC282293
0.8621	High Similarity	NPC477782
0.8556	High Similarity	NPC112654
0.8556	High Similarity	NPC319692
0.8556	High Similarity	NPC325960
0.8554	High Similarity	NPC200513
0.8539	High Similarity	NPC474555
0.8523	High Similarity	NPC165904
0.8523	High Similarity	NPC477783
0.8523	High Similarity	NPC179517
0.8506	High Similarity	NPC251528
0.8462	Intermediate Similarity	NPC204054
0.8462	Intermediate Similarity	NPC257726
0.8391	Intermediate Similarity	NPC226863
0.8391	Intermediate Similarity	NPC196407
0.8315	Intermediate Similarity	NPC141831
0.8295	Intermediate Similarity	NPC5509
0.8256	Intermediate Similarity	NPC473251
0.8256	Intermediate Similarity	NPC65661
0.8256	Intermediate Similarity	NPC42586
0.8242	Intermediate Similarity	NPC473369
0.8235	Intermediate Similarity	NPC193198
0.8235	Intermediate Similarity	NPC22611
0.8222	Intermediate Similarity	NPC166346
0.8202	Intermediate Similarity	NPC232426
0.8202	Intermediate Similarity	NPC281942
0.8191	Intermediate Similarity	NPC471075
0.8182	Intermediate Similarity	NPC472302
0.8161	Intermediate Similarity	NPC244174
0.8152	Intermediate Similarity	NPC470801
0.8105	Intermediate Similarity	NPC134077
0.8095	Intermediate Similarity	NPC195424
0.809	Intermediate Similarity	NPC174342
0.809	Intermediate Similarity	NPC470734
0.8085	Intermediate Similarity	NPC477720
0.8065	Intermediate Similarity	NPC475709
0.8065	Intermediate Similarity	NPC476768
0.8046	Intermediate Similarity	NPC86316
0.8046	Intermediate Similarity	NPC106416
0.8041	Intermediate Similarity	NPC127790
0.8022	Intermediate Similarity	NPC475657
0.8022	Intermediate Similarity	NPC471571
0.8022	Intermediate Similarity	NPC472303
0.8021	Intermediate Similarity	NPC471365
0.8021	Intermediate Similarity	NPC132395
0.8021	Intermediate Similarity	NPC471364
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC63249
0.8	Intermediate Similarity	NPC212679
0.8	Intermediate Similarity	NPC220454
0.7976	Intermediate Similarity	NPC150646
0.7957	Intermediate Similarity	NPC311166
0.7955	Intermediate Similarity	NPC220478
0.7938	Intermediate Similarity	NPC476763
0.7938	Intermediate Similarity	NPC476764
0.7931	Intermediate Similarity	NPC30486
0.7931	Intermediate Similarity	NPC149869
0.7912	Intermediate Similarity	NPC289479
0.7912	Intermediate Similarity	NPC477122
0.7907	Intermediate Similarity	NPC186276
0.7895	Intermediate Similarity	NPC473219
0.7895	Intermediate Similarity	NPC470761
0.7889	Intermediate Similarity	NPC168131
0.7889	Intermediate Similarity	NPC284561
0.7882	Intermediate Similarity	NPC474956
0.7865	Intermediate Similarity	NPC475678
0.7865	Intermediate Similarity	NPC312561
0.7857	Intermediate Similarity	NPC471220
0.7857	Intermediate Similarity	NPC476762
0.7857	Intermediate Similarity	NPC476760
0.7857	Intermediate Similarity	NPC476761
0.7849	Intermediate Similarity	NPC295347
0.7841	Intermediate Similarity	NPC300985
0.7826	Intermediate Similarity	NPC469939
0.7826	Intermediate Similarity	NPC115021
0.7826	Intermediate Similarity	NPC242069
0.7816	Intermediate Similarity	NPC477124
0.7812	Intermediate Similarity	NPC473384
0.7802	Intermediate Similarity	NPC161638
0.7802	Intermediate Similarity	NPC8062
0.7802	Intermediate Similarity	NPC51486
0.7802	Intermediate Similarity	NPC159748
0.7802	Intermediate Similarity	NPC101651
0.7791	Intermediate Similarity	NPC149237
0.7791	Intermediate Similarity	NPC229584
0.7791	Intermediate Similarity	NPC14203
0.7791	Intermediate Similarity	NPC40228
0.7778	Intermediate Similarity	NPC472810
0.7778	Intermediate Similarity	NPC472809
0.7778	Intermediate Similarity	NPC477128
0.7753	Intermediate Similarity	NPC118266
0.7742	Intermediate Similarity	NPC477129
0.7742	Intermediate Similarity	NPC298973
0.7742	Intermediate Similarity	NPC84893
0.7742	Intermediate Similarity	NPC475572
0.7742	Intermediate Similarity	NPC477130
0.7742	Intermediate Similarity	NPC88507
0.7742	Intermediate Similarity	NPC477722
0.7742	Intermediate Similarity	NPC104925
0.7732	Intermediate Similarity	NPC476769
0.7727	Intermediate Similarity	NPC475100
0.7717	Intermediate Similarity	NPC474631
0.7708	Intermediate Similarity	NPC476767
0.7701	Intermediate Similarity	NPC268122
0.7701	Intermediate Similarity	NPC471218
0.77	Intermediate Similarity	NPC325054
0.77	Intermediate Similarity	NPC90946
0.77	Intermediate Similarity	NPC300614
0.7692	Intermediate Similarity	NPC293044
0.7692	Intermediate Similarity	NPC174765
0.7684	Intermediate Similarity	NPC132753
0.7684	Intermediate Similarity	NPC38530
0.7684	Intermediate Similarity	NPC476253
0.7684	Intermediate Similarity	NPC208094
0.7684	Intermediate Similarity	NPC175351
0.7684	Intermediate Similarity	NPC121402
0.7684	Intermediate Similarity	NPC151681
0.7684	Intermediate Similarity	NPC224356
0.7684	Intermediate Similarity	NPC84335
0.7683	Intermediate Similarity	NPC476490
0.7683	Intermediate Similarity	NPC476489
0.7667	Intermediate Similarity	NPC477228
0.7653	Intermediate Similarity	NPC471208
0.7653	Intermediate Similarity	NPC476770
0.764	Intermediate Similarity	NPC471300
0.764	Intermediate Similarity	NPC177932
0.764	Intermediate Similarity	NPC474860
0.764	Intermediate Similarity	NPC30984
0.7634	Intermediate Similarity	NPC271652
0.7634	Intermediate Similarity	NPC139692
0.7634	Intermediate Similarity	NPC470576
0.7629	Intermediate Similarity	NPC472643
0.7624	Intermediate Similarity	NPC31522
0.7624	Intermediate Similarity	NPC476759
0.7624	Intermediate Similarity	NPC112457
0.7614	Intermediate Similarity	NPC469
0.7614	Intermediate Similarity	NPC118423
0.7609	Intermediate Similarity	NPC469372
0.7609	Intermediate Similarity	NPC472307
0.7582	Intermediate Similarity	NPC215831
0.7579	Intermediate Similarity	NPC472363
0.7579	Intermediate Similarity	NPC154526
0.7579	Intermediate Similarity	NPC472362
0.7576	Intermediate Similarity	NPC119493
0.7558	Intermediate Similarity	NPC327674
0.7556	Intermediate Similarity	NPC168248
0.7553	Intermediate Similarity	NPC324078
0.7553	Intermediate Similarity	NPC470697
0.7553	Intermediate Similarity	NPC469697
0.7553	Intermediate Similarity	NPC38830
0.7549	Intermediate Similarity	NPC476766
0.7529	Intermediate Similarity	NPC189206
0.7529	Intermediate Similarity	NPC472300
0.7528	Intermediate Similarity	NPC474359
0.7528	Intermediate Similarity	NPC318515
0.7527	Intermediate Similarity	NPC177037
0.7527	Intermediate Similarity	NPC472814
0.7527	Intermediate Similarity	NPC472811
0.7526	Intermediate Similarity	NPC54705
0.7526	Intermediate Similarity	NPC476299
0.7526	Intermediate Similarity	NPC110897
0.7526	Intermediate Similarity	NPC472644
0.7526	Intermediate Similarity	NPC474012
0.7525	Intermediate Similarity	NPC177524
0.7525	Intermediate Similarity	NPC476765
0.7525	Intermediate Similarity	NPC392
0.7525	Intermediate Similarity	NPC219900
0.75	Intermediate Similarity	NPC472188
0.75	Intermediate Similarity	NPC178676
0.75	Intermediate Similarity	NPC73995
0.75	Intermediate Similarity	NPC173042
0.75	Intermediate Similarity	NPC65650
0.7474	Intermediate Similarity	NPC183012
0.7474	Intermediate Similarity	NPC209355
0.7474	Intermediate Similarity	NPC293052
0.7474	Intermediate Similarity	NPC33473
0.7474	Intermediate Similarity	NPC472441
0.7473	Intermediate Similarity	NPC288952
0.7471	Intermediate Similarity	NPC473685
0.7447	Intermediate Similarity	NPC277721
0.7447	Intermediate Similarity	NPC476598
0.7447	Intermediate Similarity	NPC476597
0.7447	Intermediate Similarity	NPC267266
0.7447	Intermediate Similarity	NPC472812
0.7444	Intermediate Similarity	NPC474013
0.7444	Intermediate Similarity	NPC323765
0.7444	Intermediate Similarity	NPC2709
0.7442	Intermediate Similarity	NPC4827
0.7423	Intermediate Similarity	NPC472186
0.7423	Intermediate Similarity	NPC474440
0.7423	Intermediate Similarity	NPC318917

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 NPC71626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2005
0.2-0.3	4041
0.3-0.4	1987
0.4-0.5	560
0.5-0.6	290
0.6-0.7	72
0.7-0.8	4
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
0.8554	High Similarity	NPD4752	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1694	Approved
0.7525	Intermediate Similarity	NPD6686	Approved
0.7391	Intermediate Similarity	NPD5737	Approved
0.7391	Intermediate Similarity	NPD6672	Approved
0.7363	Intermediate Similarity	NPD6684	Approved
0.7363	Intermediate Similarity	NPD7146	Approved
0.7363	Intermediate Similarity	NPD5330	Approved
0.7363	Intermediate Similarity	NPD7521	Approved
0.7363	Intermediate Similarity	NPD7334	Approved
0.7363	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD5693	Phase 1
0.7204	Intermediate Similarity	NPD6903	Approved
0.7204	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8039	Approved
0.7087	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6673	Approved
0.6947	Remote Similarity	NPD6080	Approved
0.6947	Remote Similarity	NPD6904	Approved
0.6939	Remote Similarity	NPD5695	Phase 3
0.69	Remote Similarity	NPD7638	Approved
0.6887	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5692	Phase 3
0.6842	Remote Similarity	NPD5208	Approved
0.6837	Remote Similarity	NPD7900	Approved
0.6837	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7748	Approved
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6804	Remote Similarity	NPD5694	Approved
0.6804	Remote Similarity	NPD6050	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6771	Remote Similarity	NPD6051	Approved
0.6768	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6412	Phase 2
0.6737	Remote Similarity	NPD3573	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.6733	Remote Similarity	NPD5696	Approved
0.6701	Remote Similarity	NPD5207	Approved
0.6699	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3617	Approved
0.6638	Remote Similarity	NPD7507	Approved
0.6634	Remote Similarity	NPD7902	Approved
0.6633	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD6098	Approved
0.66	Remote Similarity	NPD5654	Approved
0.6596	Remote Similarity	NPD3666	Approved
0.6596	Remote Similarity	NPD3665	Phase 1
0.6596	Remote Similarity	NPD3133	Approved
0.6569	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD6001	Approved
0.6481	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5959	Approved
0.6471	Remote Similarity	NPD7319	Approved
0.6465	Remote Similarity	NPD5281	Approved
0.6465	Remote Similarity	NPD5284	Approved
0.6458	Remote Similarity	NPD4519	Discontinued
0.6458	Remote Similarity	NPD3618	Phase 1
0.6458	Remote Similarity	NPD4623	Approved
0.6455	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4753	Phase 2
0.6421	Remote Similarity	NPD3668	Phase 3
0.6383	Remote Similarity	NPD4221	Approved
0.6383	Remote Similarity	NPD4223	Phase 3
0.6383	Remote Similarity	NPD5209	Approved
0.6383	Remote Similarity	NPD3667	Approved
0.6373	Remote Similarity	NPD7732	Phase 3
0.6372	Remote Similarity	NPD7115	Discovery
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD6008	Approved
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6344	Remote Similarity	NPD4695	Discontinued
0.6322	Remote Similarity	NPD4137	Phase 3
0.6316	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD7327	Approved
0.6296	Remote Similarity	NPD5697	Approved
0.6296	Remote Similarity	NPD5701	Approved
0.6289	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5279	Phase 3
0.6263	Remote Similarity	NPD5328	Approved
0.6261	Remote Similarity	NPD7516	Approved
0.625	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD4747	Approved
0.625	Remote Similarity	NPD4197	Approved
0.625	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD4691	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD8377	Approved
0.6207	Remote Similarity	NPD8294	Approved
0.62	Remote Similarity	NPD5785	Approved
0.619	Remote Similarity	NPD6404	Discontinued
0.6186	Remote Similarity	NPD5329	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.618	Remote Similarity	NPD5777	Approved
0.6168	Remote Similarity	NPD6052	Approved
0.6161	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD8380	Approved
0.6154	Remote Similarity	NPD8335	Approved
0.6154	Remote Similarity	NPD8379	Approved
0.6154	Remote Similarity	NPD8296	Approved
0.6154	Remote Similarity	NPD8033	Approved
0.6154	Remote Similarity	NPD8378	Approved
0.6154	Remote Similarity	NPD7503	Approved
0.6139	Remote Similarity	NPD8035	Phase 2
0.6139	Remote Similarity	NPD6079	Approved
0.6139	Remote Similarity	NPD8034	Phase 2
0.6139	Remote Similarity	NPD6411	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD4693	Phase 3
0.6122	Remote Similarity	NPD5690	Phase 2
0.6122	Remote Similarity	NPD4694	Approved
0.6122	Remote Similarity	NPD4689	Approved
0.6122	Remote Similarity	NPD5280	Approved
0.6122	Remote Similarity	NPD5205	Approved
0.6122	Remote Similarity	NPD4138	Approved
0.6122	Remote Similarity	NPD4688	Approved
0.6122	Remote Similarity	NPD4690	Approved
0.6118	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5210	Approved
0.6117	Remote Similarity	NPD4629	Approved
0.6105	Remote Similarity	NPD4139	Approved
0.6105	Remote Similarity	NPD4692	Approved
0.6087	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6009	Approved
0.6078	Remote Similarity	NPD5779	Approved
0.6078	Remote Similarity	NPD5778	Approved
0.6078	Remote Similarity	NPD4202	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD6649	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6058	Remote Similarity	NPD4697	Phase 3
0.6058	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7614	Phase 1
0.6058	Remote Similarity	NPD5222	Approved
0.6058	Remote Similarity	NPD5221	Approved
0.605	Remote Similarity	NPD8328	Phase 3
0.6047	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4058	Approved
0.6044	Remote Similarity	NPD4687	Approved
0.6044	Remote Similarity	NPD5733	Approved
0.604	Remote Similarity	NPD46	Approved
0.604	Remote Similarity	NPD6698	Approved
0.6033	Remote Similarity	NPD8293	Discontinued
0.602	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD8297	Approved
0.6016	Remote Similarity	NPD6914	Discontinued
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD6614	Approved
0.6	Remote Similarity	NPD5276	Approved
0.5984	Remote Similarity	NPD7736	Approved
0.5978	Remote Similarity	NPD3702	Approved
0.5966	Remote Similarity	NPD6370	Approved
0.5957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6101	Approved
0.5941	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1780	Approved
0.5938	Remote Similarity	NPD1779	Approved
0.5926	Remote Similarity	NPD5211	Phase 2
0.5917	Remote Similarity	NPD6067	Discontinued
0.5888	Remote Similarity	NPD4700	Approved
0.5888	Remote Similarity	NPD5285	Approved
0.5888	Remote Similarity	NPD5286	Approved
0.5888	Remote Similarity	NPD4696	Approved
0.5868	Remote Similarity	NPD7492	Approved
0.5862	Remote Similarity	NPD7341	Phase 2
0.5862	Remote Similarity	NPD6868	Approved
0.5862	Remote Similarity	NPD6274	Approved
0.5843	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5223	Approved
0.5826	Remote Similarity	NPD7094	Approved
0.5826	Remote Similarity	NPD6858	Approved
0.5826	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD7637	Suspended
0.582	Remote Similarity	NPD6616	Approved
0.5818	Remote Similarity	NPD5141	Approved
0.5816	Remote Similarity	NPD7154	Phase 3
0.5816	Remote Similarity	NPD5362	Discontinued
0.5816	Remote Similarity	NPD4788	Approved
0.5812	Remote Similarity	NPD6317	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