NPASS Compound

Structure

NPC197461 OpenBabel07101718322D 25 29 0 0 1 0 0 0 0 0999 V2000 3.1631 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 -1.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 2.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 1.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8084 -0.7313 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 0.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8084 0.2687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 0.7687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 2.2687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 -1.2313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2029 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 11 1 0 0 0 0 4 11 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 12 21 2 0 0 0 0 13 18 1 0 0 0 0 13 22 1 1 0 0 0 14 19 1 0 0 0 0 14 23 1 6 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 18 12 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	337.19
LogP:	1.773
LogD:	1.329
LogS:	-3.588
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	4.768
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.854
MDCK Permeability:	2.9151258786441758e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	94.48248291015625%
Volume Distribution (VD):	1.021
Pgp-substrate:	5.0517449378967285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.211
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.219
CYP2C19-substrate:	0.305
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.372
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	10.542
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.926
Drug-inuced Liver Injury (DILI):	0.331
AMES Toxicity:	0.316
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.515
Skin Sensitization:	0.08
Carcinogencity:	0.876
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC197461

Natural Product ID:	NPC197461
*Common Name:**	Decaspirone G
IUPAC Name:	n.a.
Synonyms:	Decaspirone G
Standard InCHIKey:	JDOPKJKDJUPYHU-QABNGEJJSA-N
Standard InCHI:	InChI=1S/C20H18O5/c21-12-7-8-14(23)19-18(12)13(22)9-10-20(19)24-15-5-1-3-11-4-2-6-16(25-20)17(11)15/h1-6,9-10,13-14,18-19,22-23H,7-8H2/t13-,14+,18-,19+/m0/s1
SMILES:	O[C@@H]1CCC(=O)[C@@H]2[C@@H]1C1(C=C[C@@H]2O)Oc2cccc3c2c(O1)ccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465558
PubChem CID:	16099378
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33005	helicoma viridis	Species	Tubeufiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190440]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	8.0	mm	PMID[492459]
NPT1826	Organism	Lactococcus lactis	Lactococcus lactis	IZ	=	12.0	mm	PMID[492459]

☑ 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 NPC197461 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	351
0.1-0.2	1340
0.2-0.3	3051
0.3-0.4	7697
0.4-0.5	11669
0.5-0.6	4201
0.6-0.7	8777
0.7-0.8	5550
0.8-0.85	39
0.85-0.9	12
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC97662
0.9496	High Similarity	NPC257404
0.9424	High Similarity	NPC133585
0.9296	High Similarity	NPC11800
0.9296	High Similarity	NPC206579
0.9044	High Similarity	NPC284232
0.8993	High Similarity	NPC92932
0.8958	High Similarity	NPC47152
0.8889	High Similarity	NPC306816
0.8874	High Similarity	NPC472156
0.8777	High Similarity	NPC138940
0.8767	High Similarity	NPC301949
0.8699	High Similarity	NPC473951
0.8671	High Similarity	NPC193920
0.8611	High Similarity	NPC473499
0.8535	High Similarity	NPC472150
0.8516	High Similarity	NPC73148
0.8516	High Similarity	NPC472153
0.8472	Intermediate Similarity	NPC472151
0.8446	Intermediate Similarity	NPC469408
0.8418	Intermediate Similarity	NPC175082
0.8408	Intermediate Similarity	NPC74371
0.8408	Intermediate Similarity	NPC120677
0.8354	Intermediate Similarity	NPC75944
0.8269	Intermediate Similarity	NPC193749
0.8255	Intermediate Similarity	NPC472154
0.82	Intermediate Similarity	NPC288531
0.8199	Intermediate Similarity	NPC472152
0.8194	Intermediate Similarity	NPC57141
0.816	Intermediate Similarity	NPC85368
0.8153	Intermediate Similarity	NPC183402
0.8141	Intermediate Similarity	NPC469507
0.8137	Intermediate Similarity	NPC103633
0.8129	Intermediate Similarity	NPC185103
0.8125	Intermediate Similarity	NPC297404
0.8125	Intermediate Similarity	NPC11608
0.8113	Intermediate Similarity	NPC278329
0.8113	Intermediate Similarity	NPC212099
0.8113	Intermediate Similarity	NPC216752
0.8113	Intermediate Similarity	NPC146837
0.8113	Intermediate Similarity	NPC101116
0.8101	Intermediate Similarity	NPC292863
0.8101	Intermediate Similarity	NPC184326
0.8089	Intermediate Similarity	NPC177742
0.8086	Intermediate Similarity	NPC222455
0.8077	Intermediate Similarity	NPC267242
0.8067	Intermediate Similarity	NPC472155
0.8067	Intermediate Similarity	NPC151704
0.8065	Intermediate Similarity	NPC474843
0.8063	Intermediate Similarity	NPC290160
0.805	Intermediate Similarity	NPC472157
0.805	Intermediate Similarity	NPC137232
0.805	Intermediate Similarity	NPC18380
0.8039	Intermediate Similarity	NPC35150
0.8039	Intermediate Similarity	NPC106328
0.8038	Intermediate Similarity	NPC186113
0.8038	Intermediate Similarity	NPC195167
0.8025	Intermediate Similarity	NPC164244
0.8025	Intermediate Similarity	NPC63470
0.8013	Intermediate Similarity	NPC173630
0.8013	Intermediate Similarity	NPC60084
0.8013	Intermediate Similarity	NPC271076
0.8012	Intermediate Similarity	NPC178281
0.8	Intermediate Similarity	NPC39819
0.8	Intermediate Similarity	NPC3718
0.7987	Intermediate Similarity	NPC328093
0.7987	Intermediate Similarity	NPC477537
0.7987	Intermediate Similarity	NPC477535
0.7975	Intermediate Similarity	NPC246274
0.7975	Intermediate Similarity	NPC137460
0.7974	Intermediate Similarity	NPC71055
0.7964	Intermediate Similarity	NPC153578
0.7964	Intermediate Similarity	NPC277710
0.7964	Intermediate Similarity	NPC299149
0.7964	Intermediate Similarity	NPC114257
0.7963	Intermediate Similarity	NPC178173
0.7958	Intermediate Similarity	NPC470841
0.7952	Intermediate Similarity	NPC475246
0.7949	Intermediate Similarity	NPC281272
0.7939	Intermediate Similarity	NPC203751
0.7935	Intermediate Similarity	NPC475890
0.7925	Intermediate Similarity	NPC57072
0.7925	Intermediate Similarity	NPC226287
0.7925	Intermediate Similarity	NPC308265
0.7925	Intermediate Similarity	NPC231475
0.7911	Intermediate Similarity	NPC261866
0.7911	Intermediate Similarity	NPC55463
0.7911	Intermediate Similarity	NPC166116
0.7908	Intermediate Similarity	NPC211565
0.7908	Intermediate Similarity	NPC474422
0.7901	Intermediate Similarity	NPC280923
0.7901	Intermediate Similarity	NPC99216
0.7901	Intermediate Similarity	NPC474591
0.7898	Intermediate Similarity	NPC299761
0.7898	Intermediate Similarity	NPC135522
0.7898	Intermediate Similarity	NPC92153
0.7898	Intermediate Similarity	NPC230439
0.7898	Intermediate Similarity	NPC279281
0.7895	Intermediate Similarity	NPC23807
0.7892	Intermediate Similarity	NPC470667
0.7888	Intermediate Similarity	NPC56735
0.7888	Intermediate Similarity	NPC22324
0.7888	Intermediate Similarity	NPC61594
0.7888	Intermediate Similarity	NPC473961
0.7879	Intermediate Similarity	NPC30432
0.7879	Intermediate Similarity	NPC315619
0.7879	Intermediate Similarity	NPC271385
0.7879	Intermediate Similarity	NPC5029
0.7879	Intermediate Similarity	NPC111536
0.7879	Intermediate Similarity	NPC76128
0.7875	Intermediate Similarity	NPC271479
0.7875	Intermediate Similarity	NPC472618
0.7866	Intermediate Similarity	NPC259905
0.7862	Intermediate Similarity	NPC474398
0.7862	Intermediate Similarity	NPC474401
0.7862	Intermediate Similarity	NPC474441
0.7862	Intermediate Similarity	NPC476026
0.7857	Intermediate Similarity	NPC472339
0.7857	Intermediate Similarity	NPC304821
0.7853	Intermediate Similarity	NPC178851
0.7852	Intermediate Similarity	NPC265335
0.7848	Intermediate Similarity	NPC258474
0.7848	Intermediate Similarity	NPC201227
0.7844	Intermediate Similarity	NPC92403
0.7844	Intermediate Similarity	NPC46958
0.7844	Intermediate Similarity	NPC102053
0.7844	Intermediate Similarity	NPC66820
0.7844	Intermediate Similarity	NPC289876
0.7844	Intermediate Similarity	NPC76112
0.7844	Intermediate Similarity	NPC170018
0.7843	Intermediate Similarity	NPC311144
0.784	Intermediate Similarity	NPC17432
0.784	Intermediate Similarity	NPC127415
0.784	Intermediate Similarity	NPC475183
0.784	Intermediate Similarity	NPC214279
0.784	Intermediate Similarity	NPC147596
0.7838	Intermediate Similarity	NPC474610
0.7834	Intermediate Similarity	NPC473967
0.7834	Intermediate Similarity	NPC166067
0.7834	Intermediate Similarity	NPC87708
0.7831	Intermediate Similarity	NPC213052
0.7829	Intermediate Similarity	NPC474599
0.7826	Intermediate Similarity	NPC177100
0.7826	Intermediate Similarity	NPC175513
0.7826	Intermediate Similarity	NPC139540
0.7826	Intermediate Similarity	NPC472261
0.7824	Intermediate Similarity	NPC231254
0.7821	Intermediate Similarity	NPC473966
0.7821	Intermediate Similarity	NPC131874
0.7821	Intermediate Similarity	NPC93619
0.7818	Intermediate Similarity	NPC298778
0.7818	Intermediate Similarity	NPC477571
0.7818	Intermediate Similarity	NPC477573
0.7818	Intermediate Similarity	NPC477572
0.7811	Intermediate Similarity	NPC475161
0.7811	Intermediate Similarity	NPC477860
0.7808	Intermediate Similarity	NPC470160
0.7806	Intermediate Similarity	NPC146388
0.7806	Intermediate Similarity	NPC228012
0.7806	Intermediate Similarity	NPC191634
0.7806	Intermediate Similarity	NPC22137
0.78	Intermediate Similarity	NPC76312
0.78	Intermediate Similarity	NPC79372
0.7799	Intermediate Similarity	NPC309648
0.7799	Intermediate Similarity	NPC198489
0.7799	Intermediate Similarity	NPC61112
0.7799	Intermediate Similarity	NPC69531
0.7799	Intermediate Similarity	NPC32867
0.7792	Intermediate Similarity	NPC299011
0.7792	Intermediate Similarity	NPC469758
0.7792	Intermediate Similarity	NPC60389
0.7791	Intermediate Similarity	NPC222531
0.7785	Intermediate Similarity	NPC29763
0.7785	Intermediate Similarity	NPC83283
0.7785	Intermediate Similarity	NPC210003
0.7785	Intermediate Similarity	NPC39360
0.7785	Intermediate Similarity	NPC299435
0.7785	Intermediate Similarity	NPC260604
0.7785	Intermediate Similarity	NPC143851
0.7784	Intermediate Similarity	NPC307754
0.7784	Intermediate Similarity	NPC474345
0.7784	Intermediate Similarity	NPC68381
0.7784	Intermediate Similarity	NPC223735
0.7784	Intermediate Similarity	NPC186800
0.7778	Intermediate Similarity	NPC77660
0.7778	Intermediate Similarity	NPC87583
0.7778	Intermediate Similarity	NPC189142
0.7778	Intermediate Similarity	NPC113770
0.7778	Intermediate Similarity	NPC477528
0.7778	Intermediate Similarity	NPC326278
0.7778	Intermediate Similarity	NPC310603
0.7778	Intermediate Similarity	NPC15374
0.7771	Intermediate Similarity	NPC232645
0.7771	Intermediate Similarity	NPC148945
0.7771	Intermediate Similarity	NPC72958
0.7771	Intermediate Similarity	NPC204561
0.7771	Intermediate Similarity	NPC316960
0.7771	Intermediate Similarity	NPC309512
0.7771	Intermediate Similarity	NPC207346
0.7771	Intermediate Similarity	NPC233467

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 NPC197461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	834
0.2-0.3	1515
0.3-0.4	2549
0.4-0.5	2057
0.5-0.6	1223
0.6-0.7	544
0.7-0.8	128
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD3787	Discontinued
0.8365	Intermediate Similarity	NPD3751	Discontinued
0.8105	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD8313	Approved
0.7844	Intermediate Similarity	NPD8312	Approved
0.775	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2346	Discontinued
0.7722	Intermediate Similarity	NPD37	Approved
0.7716	Intermediate Similarity	NPD6959	Discontinued
0.7692	Intermediate Similarity	NPD2797	Approved
0.7688	Intermediate Similarity	NPD4967	Phase 2
0.7688	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4966	Approved
0.7673	Intermediate Similarity	NPD8455	Phase 2
0.7671	Intermediate Similarity	NPD3268	Approved
0.7651	Intermediate Similarity	NPD7054	Approved
0.7625	Intermediate Similarity	NPD5402	Approved
0.7605	Intermediate Similarity	NPD7472	Approved
0.7605	Intermediate Similarity	NPD7074	Phase 3
0.759	Intermediate Similarity	NPD7228	Approved
0.7582	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD7819	Suspended
0.756	Intermediate Similarity	NPD6797	Phase 2
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7534	Intermediate Similarity	NPD4908	Phase 1
0.7533	Intermediate Similarity	NPD7097	Phase 1
0.7517	Intermediate Similarity	NPD2798	Approved
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6166	Phase 2
0.747	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1549	Phase 2
0.744	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5844	Phase 1
0.7432	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6798	Discontinued
0.7432	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2313	Discontinued
0.7423	Intermediate Similarity	NPD3749	Approved
0.7421	Intermediate Similarity	NPD3226	Approved
0.7413	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1091	Approved
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7405	Intermediate Similarity	NPD5403	Approved
0.74	Intermediate Similarity	NPD6355	Discontinued
0.7397	Intermediate Similarity	NPD5647	Approved
0.7391	Intermediate Similarity	NPD6844	Discontinued
0.7391	Intermediate Similarity	NPD1934	Approved
0.7383	Intermediate Similarity	NPD6233	Phase 2
0.7375	Intermediate Similarity	NPD4380	Phase 2
0.7368	Intermediate Similarity	NPD3748	Approved
0.7368	Intermediate Similarity	NPD2799	Discontinued
0.7365	Intermediate Similarity	NPD4625	Phase 3
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7347	Intermediate Similarity	NPD2861	Phase 2
0.7342	Intermediate Similarity	NPD6273	Approved
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.733	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD3266	Approved
0.7329	Intermediate Similarity	NPD7411	Suspended
0.7329	Intermediate Similarity	NPD3267	Approved
0.7324	Intermediate Similarity	NPD5585	Approved
0.732	Intermediate Similarity	NPD2935	Discontinued
0.731	Intermediate Similarity	NPD7240	Approved
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6832	Phase 2
0.7292	Intermediate Similarity	NPD1610	Phase 2
0.729	Intermediate Similarity	NPD6674	Discontinued
0.7285	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1933	Approved
0.7278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5401	Approved
0.7262	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1283	Approved
0.726	Intermediate Similarity	NPD3225	Approved
0.7256	Intermediate Similarity	NPD7768	Phase 2
0.7244	Intermediate Similarity	NPD7003	Approved
0.7241	Intermediate Similarity	NPD1608	Approved
0.7239	Intermediate Similarity	NPD2801	Approved
0.7237	Intermediate Similarity	NPD6653	Approved
0.7229	Intermediate Similarity	NPD5494	Approved
0.7226	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1613	Approved
0.7219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4140	Approved
0.7219	Intermediate Similarity	NPD2979	Phase 3
0.7219	Intermediate Similarity	NPD7473	Discontinued
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1511	Approved
0.7208	Intermediate Similarity	NPD2796	Approved
0.7208	Intermediate Similarity	NPD1551	Phase 2
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.7203	Intermediate Similarity	NPD1651	Approved
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4749	Approved
0.7188	Intermediate Similarity	NPD7427	Discontinued
0.7171	Intermediate Similarity	NPD447	Suspended
0.7171	Intermediate Similarity	NPD4618	Approved
0.7171	Intermediate Similarity	NPD4622	Approved
0.7161	Intermediate Similarity	NPD6002	Phase 3
0.7161	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6004	Phase 3
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6005	Phase 3
0.7161	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8032	Phase 2
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7134	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1894	Discontinued
0.7125	Intermediate Similarity	NPD1512	Approved
0.7123	Intermediate Similarity	NPD9717	Approved
0.7115	Intermediate Similarity	NPD2897	Discontinued
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7103	Intermediate Similarity	NPD3496	Discontinued
0.7097	Intermediate Similarity	NPD2438	Suspended
0.7097	Intermediate Similarity	NPD6032	Approved
0.7097	Intermediate Similarity	NPD4476	Approved
0.7097	Intermediate Similarity	NPD4477	Approved
0.7091	Intermediate Similarity	NPD3817	Phase 2
0.7086	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5689	Approved
0.7078	Intermediate Similarity	NPD5688	Approved
0.7075	Intermediate Similarity	NPD4359	Approved
0.707	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1611	Approved
0.7055	Intermediate Similarity	NPD1535	Discovery
0.7055	Intermediate Similarity	NPD1281	Approved
0.7051	Intermediate Similarity	NPD2344	Approved
0.7051	Intermediate Similarity	NPD5763	Approved
0.7051	Intermediate Similarity	NPD5762	Approved
0.7049	Intermediate Similarity	NPD6782	Approved
0.7049	Intermediate Similarity	NPD6780	Approved
0.7049	Intermediate Similarity	NPD6778	Approved
0.7049	Intermediate Similarity	NPD6781	Approved
0.7049	Intermediate Similarity	NPD6779	Approved
0.7049	Intermediate Similarity	NPD6776	Approved
0.7049	Intermediate Similarity	NPD6777	Approved
0.7048	Intermediate Similarity	NPD3882	Suspended
0.7042	Intermediate Similarity	NPD6671	Approved
0.7042	Intermediate Similarity	NPD709	Approved
0.7034	Intermediate Similarity	NPD17	Approved
0.7034	Intermediate Similarity	NPD1778	Approved
0.7032	Intermediate Similarity	NPD4308	Phase 3
0.7032	Intermediate Similarity	NPD4108	Discontinued
0.703	Intermediate Similarity	NPD1465	Phase 2
0.702	Intermediate Similarity	NPD7095	Approved
0.7014	Intermediate Similarity	NPD1548	Phase 1
0.7007	Intermediate Similarity	NPD2231	Phase 2
0.7007	Intermediate Similarity	NPD2235	Phase 2
0.7007	Intermediate Similarity	NPD1481	Phase 2
0.7006	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD6799	Approved
0.698	Remote Similarity	NPD6362	Approved
0.698	Remote Similarity	NPD1470	Approved
0.6974	Remote Similarity	NPD411	Approved
0.6973	Remote Similarity	NPD6823	Phase 2
0.697	Remote Similarity	NPD6801	Discontinued
0.6968	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2534	Approved
0.6954	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5124	Phase 1
0.6948	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7783	Phase 2
0.6947	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1201	Approved
0.6935	Remote Similarity	NPD7697	Approved
0.6935	Remote Similarity	NPD7696	Phase 3
0.6935	Remote Similarity	NPD7698	Approved
0.6935	Remote Similarity	NPD7435	Discontinued
0.6933	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1653	Approved
0.6928	Remote Similarity	NPD4870	Approved
0.6928	Remote Similarity	NPD4062	Phase 3

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