NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	488.24
Volume:	501.745
LogP:	4.117
LogD:	3.095
LogS:	-3.757
# Rotatable Bonds:	7
TPSA:	112.27
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	5.297
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.901
MDCK Permeability:	4.355672717792913e-05
Pgp-inhibitor:	0.595
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.678
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	90.83657836914062%
Volume Distribution (VD):	2.084
Pgp-substrate:	8.326859474182129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.411
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.56
CYP2C9-substrate:	0.274
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.469
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	3.991
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.426
Skin Sensitization:	0.542
Carcinogencity:	0.055
Eye Corrosion:	0.007
Eye Irritation:	0.014
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC476599

Natural Product ID:	NPC476599
*Common Name:**	Anthoptilide D
IUPAC Name:	[(1S,7S,8Z,12R,13S,14R)-14-acetyloxy-4,9,13,17-tetramethyl-5,15-dioxo-6-oxatricyclo[11.4.0.03,7]heptadeca-3,8,16-trien-12-yl] benzoate
Synonyms:	Anthoptilide D
Standard InCHIKey:	IQXHMLGCACSFNA-KSADDXLTSA-N
Standard InCHI:	InChI=1S/C29H32O7/c1-16-11-12-25(36-28(33)20-9-7-6-8-10-20)29(5)22(15-21-18(3)27(32)35-24(21)13-16)17(2)14-23(31)26(29)34-19(4)30/h6-10,13-14,22,24-26H,11-12,15H2,1-5H3/b16-13-/t22-,24-,25+,26-,29-/m0/s1
SMILES:	C/C/1=C/[C@H]2C(=C(C(=O)O2)C)C[C@H]3C(=CC(=O)[C@@H]([C@@]3([C@@H](CC1)OC(=O)C4=CC=CC=C4)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	21775682
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
NPO33618	Anthoptilum cf. kukenthali	Species	Anthoptilidae	Eukaryota	n.a.	at the depth of 267 m from CSIRO RV Southern Surveyor, on the Northwest side of Port Hedland (18.16.6 S, 118.11.2 E), Western Australia	n.a.	PMID[10757710]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	IC50	=	500000	nM	PMID[10757710]

☑ 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 NPC476599 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	1203
0.2-0.3	2604
0.3-0.4	6532
0.4-0.5	12013
0.5-0.6	13586
0.6-0.7	5644
0.7-0.8	774
0.8-0.85	63
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC50872
0.9167	High Similarity	NPC473243
0.8615	High Similarity	NPC238370
0.8475	Intermediate Similarity	NPC469636
0.8462	Intermediate Similarity	NPC42234
0.843	Intermediate Similarity	NPC307651
0.8372	Intermediate Similarity	NPC169913
0.8346	Intermediate Similarity	NPC203486
0.8333	Intermediate Similarity	NPC477360
0.8333	Intermediate Similarity	NPC472394
0.8321	Intermediate Similarity	NPC472546
0.8321	Intermediate Similarity	NPC471832
0.8321	Intermediate Similarity	NPC473247
0.8321	Intermediate Similarity	NPC147561
0.8295	Intermediate Similarity	NPC275576
0.8271	Intermediate Similarity	NPC472656
0.8264	Intermediate Similarity	NPC270699
0.8264	Intermediate Similarity	NPC82899
0.8258	Intermediate Similarity	NPC470278
0.8222	Intermediate Similarity	NPC472545
0.8222	Intermediate Similarity	NPC477358
0.8222	Intermediate Similarity	NPC472551
0.8217	Intermediate Similarity	NPC295664
0.8209	Intermediate Similarity	NPC477368
0.8209	Intermediate Similarity	NPC329913
0.8197	Intermediate Similarity	NPC161611
0.8197	Intermediate Similarity	NPC128368
0.8188	Intermediate Similarity	NPC182869
0.8182	Intermediate Similarity	NPC305912
0.8182	Intermediate Similarity	NPC1082
0.8182	Intermediate Similarity	NPC272946
0.8175	Intermediate Similarity	NPC204784
0.8175	Intermediate Similarity	NPC251294
0.8167	Intermediate Similarity	NPC83628
0.8167	Intermediate Similarity	NPC265407
0.8162	Intermediate Similarity	NPC39549
0.8148	Intermediate Similarity	NPC232888
0.8148	Intermediate Similarity	NPC473399
0.8148	Intermediate Similarity	NPC265459
0.8148	Intermediate Similarity	NPC475262
0.8148	Intermediate Similarity	NPC477367
0.8148	Intermediate Similarity	NPC473216
0.8148	Intermediate Similarity	NPC290833
0.8148	Intermediate Similarity	NPC270364
0.8145	Intermediate Similarity	NPC226093
0.8145	Intermediate Similarity	NPC149691
0.8143	Intermediate Similarity	NPC471100
0.8143	Intermediate Similarity	NPC471107
0.8134	Intermediate Similarity	NPC477364
0.811	Intermediate Similarity	NPC77000
0.811	Intermediate Similarity	NPC238861
0.8102	Intermediate Similarity	NPC276652
0.8099	Intermediate Similarity	NPC196246
0.8099	Intermediate Similarity	NPC251854
0.8099	Intermediate Similarity	NPC214067
0.8099	Intermediate Similarity	NPC93084
0.8092	Intermediate Similarity	NPC470753
0.8092	Intermediate Similarity	NPC473220
0.8092	Intermediate Similarity	NPC51292
0.8088	Intermediate Similarity	NPC194769
0.8088	Intermediate Similarity	NPC285221
0.8085	Intermediate Similarity	NPC475552
0.8074	Intermediate Similarity	NPC126516
0.8074	Intermediate Similarity	NPC472250
0.8074	Intermediate Similarity	NPC474608
0.8074	Intermediate Similarity	NPC477359
0.8071	Intermediate Similarity	NPC470231
0.8065	Intermediate Similarity	NPC470764
0.8058	Intermediate Similarity	NPC183540
0.8051	Intermediate Similarity	NPC301943
0.8051	Intermediate Similarity	NPC474365
0.8043	Intermediate Similarity	NPC475400
0.8043	Intermediate Similarity	NPC477904
0.8043	Intermediate Similarity	NPC472547
0.8043	Intermediate Similarity	NPC183270
0.8043	Intermediate Similarity	NPC475660
0.8033	Intermediate Similarity	NPC474157
0.8033	Intermediate Similarity	NPC210089
0.8029	Intermediate Similarity	NPC86772
0.8029	Intermediate Similarity	NPC475373
0.8017	Intermediate Similarity	NPC10251
0.8017	Intermediate Similarity	NPC17417
0.8015	Intermediate Similarity	NPC472577
0.8015	Intermediate Similarity	NPC195647
0.8015	Intermediate Similarity	NPC17877
0.8015	Intermediate Similarity	NPC470765
0.8015	Intermediate Similarity	NPC66761
0.8015	Intermediate Similarity	NPC291638
0.8015	Intermediate Similarity	NPC79699
0.8015	Intermediate Similarity	NPC472247
0.8	Intermediate Similarity	NPC153214
0.8	Intermediate Similarity	NPC51079
0.7986	Intermediate Similarity	NPC224491
0.7986	Intermediate Similarity	NPC473654
0.7985	Intermediate Similarity	NPC469519
0.7984	Intermediate Similarity	NPC477411
0.7984	Intermediate Similarity	NPC241851
0.7972	Intermediate Similarity	NPC473403
0.7971	Intermediate Similarity	NPC472395
0.7971	Intermediate Similarity	NPC325805
0.7971	Intermediate Similarity	NPC472371
0.7971	Intermediate Similarity	NPC272523
0.7941	Intermediate Similarity	NPC48929
0.7934	Intermediate Similarity	NPC56493
0.7926	Intermediate Similarity	NPC469499
0.7926	Intermediate Similarity	NPC475569
0.792	Intermediate Similarity	NPC210092
0.792	Intermediate Similarity	NPC474095
0.7917	Intermediate Similarity	NPC254558
0.7917	Intermediate Similarity	NPC125033
0.7907	Intermediate Similarity	NPC144547
0.7903	Intermediate Similarity	NPC474176
0.7899	Intermediate Similarity	NPC283375
0.7899	Intermediate Similarity	NPC183122
0.7895	Intermediate Similarity	NPC472707
0.7887	Intermediate Similarity	NPC127857
0.7883	Intermediate Similarity	NPC477896
0.7883	Intermediate Similarity	NPC477893
0.7883	Intermediate Similarity	NPC474659
0.7883	Intermediate Similarity	NPC23894
0.7872	Intermediate Similarity	NPC82467
0.7869	Intermediate Similarity	NPC474364
0.7863	Intermediate Similarity	NPC8990
0.7863	Intermediate Similarity	NPC472704
0.7863	Intermediate Similarity	NPC328107
0.7862	Intermediate Similarity	NPC471103
0.7862	Intermediate Similarity	NPC101043
0.7862	Intermediate Similarity	NPC306799
0.7862	Intermediate Similarity	NPC51602
0.7857	Intermediate Similarity	NPC473497
0.7852	Intermediate Similarity	NPC72915
0.7851	Intermediate Similarity	NPC119271
0.7847	Intermediate Similarity	NPC473215
0.7842	Intermediate Similarity	NPC475652
0.7842	Intermediate Similarity	NPC210591
0.7842	Intermediate Similarity	NPC214550
0.784	Intermediate Similarity	NPC196075
0.784	Intermediate Similarity	NPC153053
0.7829	Intermediate Similarity	NPC289432
0.7829	Intermediate Similarity	NPC988
0.7826	Intermediate Similarity	NPC472372
0.7826	Intermediate Similarity	NPC472374
0.781	Intermediate Similarity	NPC298547
0.781	Intermediate Similarity	NPC324898
0.781	Intermediate Similarity	NPC134937
0.781	Intermediate Similarity	NPC153617
0.7805	Intermediate Similarity	NPC174099
0.7803	Intermediate Similarity	NPC477369
0.7801	Intermediate Similarity	NPC475135
0.7797	Intermediate Similarity	NPC146351
0.7794	Intermediate Similarity	NPC471880
0.7793	Intermediate Similarity	NPC473214
0.7793	Intermediate Similarity	NPC470245
0.7786	Intermediate Similarity	NPC90614
0.7786	Intermediate Similarity	NPC275592
0.7786	Intermediate Similarity	NPC43241
0.7786	Intermediate Similarity	NPC473112
0.7786	Intermediate Similarity	NPC147880
0.7786	Intermediate Similarity	NPC473085
0.7786	Intermediate Similarity	NPC473081
0.7786	Intermediate Similarity	NPC171207
0.7786	Intermediate Similarity	NPC473109
0.7786	Intermediate Similarity	NPC472703
0.7786	Intermediate Similarity	NPC48017
0.7786	Intermediate Similarity	NPC184747
0.7786	Intermediate Similarity	NPC100913
0.7786	Intermediate Similarity	NPC473613
0.7786	Intermediate Similarity	NPC211137
0.7786	Intermediate Similarity	NPC97667
0.7786	Intermediate Similarity	NPC473758
0.7786	Intermediate Similarity	NPC473060
0.7786	Intermediate Similarity	NPC200592
0.7786	Intermediate Similarity	NPC476094
0.7786	Intermediate Similarity	NPC4341
0.7778	Intermediate Similarity	NPC475508
0.7761	Intermediate Similarity	NPC195224
0.7761	Intermediate Similarity	NPC115797
0.7761	Intermediate Similarity	NPC51448
0.7755	Intermediate Similarity	NPC219419
0.7754	Intermediate Similarity	NPC279637
0.7754	Intermediate Similarity	NPC149401
0.775	Intermediate Similarity	NPC89886
0.7746	Intermediate Similarity	NPC477096
0.7746	Intermediate Similarity	NPC91703
0.7746	Intermediate Similarity	NPC95449
0.7746	Intermediate Similarity	NPC45307
0.7746	Intermediate Similarity	NPC477468
0.7746	Intermediate Similarity	NPC477094
0.7744	Intermediate Similarity	NPC121272
0.774	Intermediate Similarity	NPC472398
0.7734	Intermediate Similarity	NPC152812
0.773	Intermediate Similarity	NPC187566
0.773	Intermediate Similarity	NPC97947
0.773	Intermediate Similarity	NPC87448
0.773	Intermediate Similarity	NPC291599
0.773	Intermediate Similarity	NPC118080
0.773	Intermediate Similarity	NPC472576
0.773	Intermediate Similarity	NPC475413
0.773	Intermediate Similarity	NPC474303
0.773	Intermediate Similarity	NPC16912

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 NPC476599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	853
0.2-0.3	1400
0.3-0.4	2712
0.4-0.5	2401
0.5-0.6	1199
0.6-0.7	327
0.7-0.8	23
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
0.8333	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD7236	Approved
0.811	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD2182	Approved
0.7862	Intermediate Similarity	NPD7239	Suspended
0.7805	Intermediate Similarity	NPD2067	Discontinued
0.7724	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD164	Approved
0.7647	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6287	Discontinued
0.75	Intermediate Similarity	NPD1238	Approved
0.75	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2629	Approved
0.748	Intermediate Similarity	NPD7094	Approved
0.748	Intermediate Similarity	NPD6858	Approved
0.741	Intermediate Similarity	NPD7961	Discontinued
0.7402	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7008	Discontinued
0.7386	Intermediate Similarity	NPD7057	Phase 3
0.7386	Intermediate Similarity	NPD7058	Phase 2
0.7308	Intermediate Similarity	NPD4198	Discontinued
0.7231	Intermediate Similarity	NPD5951	Approved
0.7177	Intermediate Similarity	NPD1929	Approved
0.7177	Intermediate Similarity	NPD1930	Approved
0.7177	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6647	Phase 2
0.7174	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1237	Approved
0.7081	Intermediate Similarity	NPD7799	Discontinued
0.7063	Intermediate Similarity	NPD6355	Discontinued
0.7055	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6085	Phase 2
0.705	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2799	Discontinued
0.7029	Intermediate Similarity	NPD1876	Approved
0.7027	Intermediate Similarity	NPD8166	Discontinued
0.702	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD3972	Approved
0.6993	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3764	Approved
0.6966	Remote Similarity	NPD2567	Approved
0.6966	Remote Similarity	NPD2569	Approved
0.695	Remote Similarity	NPD6832	Phase 2
0.6942	Remote Similarity	NPD1202	Approved
0.6942	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2066	Phase 3
0.6923	Remote Similarity	NPD7713	Phase 3
0.6923	Remote Similarity	NPD8032	Phase 2
0.6913	Remote Similarity	NPD4628	Phase 3
0.6909	Remote Similarity	NPD8368	Discontinued
0.6906	Remote Similarity	NPD5667	Approved
0.6894	Remote Similarity	NPD1241	Discontinued
0.6886	Remote Similarity	NPD8407	Phase 2
0.6867	Remote Similarity	NPD3887	Approved
0.686	Remote Similarity	NPD7631	Approved
0.685	Remote Similarity	NPD5909	Discontinued
0.6839	Remote Similarity	NPD6599	Discontinued
0.6829	Remote Similarity	NPD1989	Approved
0.6824	Remote Similarity	NPD1471	Phase 3
0.6815	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6663	Approved
0.6803	Remote Similarity	NPD7305	Phase 1
0.6803	Remote Similarity	NPD3748	Approved
0.68	Remote Similarity	NPD7003	Approved
0.6786	Remote Similarity	NPD2199	Approved
0.6786	Remote Similarity	NPD2198	Approved
0.6783	Remote Similarity	NPD6039	Approved
0.678	Remote Similarity	NPD9259	Approved
0.678	Remote Similarity	NPD9257	Approved
0.6777	Remote Similarity	NPD7609	Phase 3
0.6774	Remote Similarity	NPD3495	Discontinued
0.6774	Remote Similarity	NPD7458	Discontinued
0.6767	Remote Similarity	NPD6010	Discontinued
0.6765	Remote Similarity	NPD7741	Discontinued
0.6765	Remote Similarity	NPD9545	Approved
0.6763	Remote Similarity	NPD6637	Approved
0.6761	Remote Similarity	NPD5736	Approved
0.6759	Remote Similarity	NPD2979	Phase 3
0.6757	Remote Similarity	NPD2438	Suspended
0.675	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2313	Discontinued
0.6727	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.672	Remote Similarity	NPD9495	Approved
0.6716	Remote Similarity	NPD4766	Approved
0.6713	Remote Similarity	NPD7055	Discontinued
0.6711	Remote Similarity	NPD2346	Discontinued
0.6706	Remote Similarity	NPD8434	Phase 2
0.6706	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3673	Approved
0.6694	Remote Similarity	NPD3672	Approved
0.6693	Remote Similarity	NPD1932	Approved
0.6691	Remote Similarity	NPD1281	Approved
0.6691	Remote Similarity	NPD4807	Approved
0.6691	Remote Similarity	NPD7610	Discontinued
0.6691	Remote Similarity	NPD4806	Approved
0.669	Remote Similarity	NPD2798	Approved
0.669	Remote Similarity	NPD2788	Approved
0.6687	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD7798	Approved
0.6667	Remote Similarity	NPD5306	Approved
0.6644	Remote Similarity	NPD2935	Discontinued
0.6641	Remote Similarity	NPD2329	Discontinued
0.6628	Remote Similarity	NPD8435	Approved
0.6623	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6798	Discontinued
0.662	Remote Similarity	NPD3267	Approved
0.662	Remote Similarity	NPD3266	Approved
0.6618	Remote Similarity	NPD9493	Approved
0.6617	Remote Similarity	NPD969	Suspended
0.6615	Remote Similarity	NPD3134	Approved
0.6615	Remote Similarity	NPD6685	Approved
0.6613	Remote Similarity	NPD1693	Approved
0.6604	Remote Similarity	NPD7819	Suspended
0.66	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2353	Approved
0.6594	Remote Similarity	NPD5585	Approved
0.6594	Remote Similarity	NPD5691	Approved
0.6594	Remote Similarity	NPD3025	Approved
0.6594	Remote Similarity	NPD3024	Approved
0.6585	Remote Similarity	NPD1088	Approved
0.6583	Remote Similarity	NPD1087	Approved
0.6579	Remote Similarity	NPD3750	Approved
0.6579	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6233	Phase 2
0.6571	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2347	Approved
0.6569	Remote Similarity	NPD6065	Approved
0.6561	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD9256	Approved
0.6557	Remote Similarity	NPD9258	Approved
0.6556	Remote Similarity	NPD4534	Discontinued
0.6554	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7095	Approved
0.6549	Remote Similarity	NPD1283	Approved
0.6547	Remote Similarity	NPD2932	Approved
0.6541	Remote Similarity	NPD6801	Discontinued
0.6533	Remote Similarity	NPD2531	Phase 2
0.6533	Remote Similarity	NPD2796	Approved
0.6532	Remote Similarity	NPD8360	Approved
0.6532	Remote Similarity	NPD8361	Approved
0.6531	Remote Similarity	NPD4307	Phase 2
0.6531	Remote Similarity	NPD3373	Approved
0.6522	Remote Similarity	NPD7009	Phase 2
0.6512	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6765	Approved
0.6509	Remote Similarity	NPD6764	Approved
0.6507	Remote Similarity	NPD3268	Approved
0.6503	Remote Similarity	NPD2797	Approved
0.65	Remote Similarity	NPD3026	Approved
0.65	Remote Similarity	NPD4136	Approved
0.65	Remote Similarity	NPD4135	Approved
0.65	Remote Similarity	NPD4106	Approved
0.65	Remote Similarity	NPD3023	Approved
0.6486	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6873	Phase 2
0.6475	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1651	Approved
0.6474	Remote Similarity	NPD5049	Phase 3
0.6471	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4110	Phase 3
0.6466	Remote Similarity	NPD5239	Approved
0.6466	Remote Similarity	NPD5235	Approved
0.6466	Remote Similarity	NPD5240	Approved
0.6466	Remote Similarity	NPD1317	Discontinued
0.6466	Remote Similarity	NPD4234	Approved
0.6466	Remote Similarity	NPD4233	Approved
0.6466	Remote Similarity	NPD5236	Approved
0.6466	Remote Similarity	NPD5237	Approved
0.6463	Remote Similarity	NPD4062	Phase 3
0.6458	Remote Similarity	NPD1019	Discontinued
0.6457	Remote Similarity	NPD5926	Approved
0.6447	Remote Similarity	NPD2897	Discontinued
0.6447	Remote Similarity	NPD5958	Discontinued
0.6446	Remote Similarity	NPD1282	Approved
0.6446	Remote Similarity	NPD650	Approved
0.6444	Remote Similarity	NPD2607	Approved
0.6439	Remote Similarity	NPD1358	Approved
0.6433	Remote Similarity	NPD920	Approved
0.6433	Remote Similarity	NPD5403	Approved
0.6429	Remote Similarity	NPD17	Approved
0.6429	Remote Similarity	NPD2354	Approved
0.6429	Remote Similarity	NPD3019	Approved
0.6423	Remote Similarity	NPD1090	Approved
0.6423	Remote Similarity	NPD1086	Approved
0.6423	Remote Similarity	NPD1089	Approved
0.6419	Remote Similarity	NPD4140	Approved
0.6419	Remote Similarity	NPD4060	Phase 1
0.6418	Remote Similarity	NPD2201	Approved
0.6414	Remote Similarity	NPD3662	Phase 3
0.6414	Remote Similarity	NPD5204	Approved
0.6414	Remote Similarity	NPD3664	Approved
0.6414	Remote Similarity	NPD3661	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