NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	4.463
LogD:	3.333
LogS:	-4.296
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	3.686
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.856
MDCK Permeability:	1.8880888092098758e-05
Pgp-inhibitor:	0.591
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.563

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	99.0860366821289%
Volume Distribution (VD):	1.927
Pgp-substrate:	2.6238794326782227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.665
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.423
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.777
CYP2D6-inhibitor:	0.528
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.674

ADMET: Excretion

Clearance (CL):	4.924
Half-life (T1/2):	0.419

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.553
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.703
Carcinogencity:	0.776
Eye Corrosion:	0.004
Eye Irritation:	0.79
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC138438

Natural Product ID:	NPC138438
*Common Name:**	Ficuseptamine B
IUPAC Name:	6-(dimethylamino)-1-(3-hydroxy-4-methoxyphenyl)hexan-1-one
Synonyms:	ficuseptamine B
Standard InCHIKey:	KHPBRJKLVIUPRG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H23NO3/c1-16(2)10-6-4-5-7-13(17)12-8-9-15(19-3)14(18)11-12/h8-9,11,18H,4-7,10H2,1-3H3
SMILES:	COc1ccc(cc1O)C(=O)CCCCCN(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088609
PubChem CID:	44614017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	Stems	Tainan Hsien, Taiwan, Republic of China	2000-JAN	PMID[16038551]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19938815]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	23000.0	nM	PMID[557153]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	72000.0	nM	PMID[557153]

☑ 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 NPC138438 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	217
0.1-0.2	1174
0.2-0.3	4904
0.3-0.4	12185
0.4-0.5	4993
0.5-0.6	6064
0.6-0.7	10442
0.7-0.8	2603
0.8-0.85	97
0.85-0.9	13
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC908
0.95	High Similarity	NPC469540
0.95	High Similarity	NPC469539
0.9023	High Similarity	NPC16651
0.9023	High Similarity	NPC32163
0.8759	High Similarity	NPC153644
0.8696	High Similarity	NPC50763
0.8647	High Similarity	NPC114298
0.8603	High Similarity	NPC117237
0.8603	High Similarity	NPC203719
0.8582	High Similarity	NPC4181
0.8582	High Similarity	NPC164778
0.8582	High Similarity	NPC474691
0.8582	High Similarity	NPC257976
0.8582	High Similarity	NPC242372
0.8552	High Similarity	NPC469978
0.8551	High Similarity	NPC66905
0.8519	High Similarity	NPC273686
0.8519	High Similarity	NPC312404
0.8511	High Similarity	NPC139519
0.8496	Intermediate Similarity	NPC225245
0.8433	Intermediate Similarity	NPC201777
0.8431	Intermediate Similarity	NPC135006
0.8429	Intermediate Similarity	NPC111888
0.8417	Intermediate Similarity	NPC298268
0.8394	Intermediate Similarity	NPC179777
0.8392	Intermediate Similarity	NPC231572
0.8387	Intermediate Similarity	NPC35345
0.838	Intermediate Similarity	NPC208760
0.838	Intermediate Similarity	NPC204592
0.8369	Intermediate Similarity	NPC159418
0.8369	Intermediate Similarity	NPC283823
0.8356	Intermediate Similarity	NPC192597
0.8356	Intermediate Similarity	NPC176030
0.8356	Intermediate Similarity	NPC141817
0.8356	Intermediate Similarity	NPC229218
0.8356	Intermediate Similarity	NPC169214
0.8346	Intermediate Similarity	NPC299406
0.8345	Intermediate Similarity	NPC304622
0.8333	Intermediate Similarity	NPC325625
0.8333	Intermediate Similarity	NPC5018
0.8333	Intermediate Similarity	NPC123228
0.8333	Intermediate Similarity	NPC123722
0.8333	Intermediate Similarity	NPC276466
0.8333	Intermediate Similarity	NPC151167
0.8322	Intermediate Similarity	NPC470088
0.8309	Intermediate Similarity	NPC163083
0.8299	Intermediate Similarity	NPC239608
0.8299	Intermediate Similarity	NPC46161
0.8299	Intermediate Similarity	NPC46880
0.8286	Intermediate Similarity	NPC172673
0.8261	Intermediate Similarity	NPC90128
0.8261	Intermediate Similarity	NPC84076
0.8261	Intermediate Similarity	NPC303680
0.8243	Intermediate Similarity	NPC207732
0.8239	Intermediate Similarity	NPC327410
0.8222	Intermediate Similarity	NPC158949
0.8195	Intermediate Similarity	NPC150919
0.8188	Intermediate Similarity	NPC257589
0.8188	Intermediate Similarity	NPC53305
0.8182	Intermediate Similarity	NPC144662
0.8176	Intermediate Similarity	NPC50954
0.8176	Intermediate Similarity	NPC469615
0.8169	Intermediate Similarity	NPC239302
0.8163	Intermediate Similarity	NPC84273
0.8156	Intermediate Similarity	NPC285776
0.8151	Intermediate Similarity	NPC4796
0.8146	Intermediate Similarity	NPC478189
0.8129	Intermediate Similarity	NPC127937
0.8129	Intermediate Similarity	NPC92207
0.8121	Intermediate Similarity	NPC469683
0.8116	Intermediate Similarity	NPC30216
0.8108	Intermediate Similarity	NPC312256
0.8095	Intermediate Similarity	NPC28398
0.8095	Intermediate Similarity	NPC50823
0.8088	Intermediate Similarity	NPC295317
0.8085	Intermediate Similarity	NPC261759
0.8082	Intermediate Similarity	NPC284409
0.8071	Intermediate Similarity	NPC286683
0.8071	Intermediate Similarity	NPC281020
0.8071	Intermediate Similarity	NPC20404
0.8071	Intermediate Similarity	NPC12022
0.8071	Intermediate Similarity	NPC293641
0.8071	Intermediate Similarity	NPC20287
0.8069	Intermediate Similarity	NPC324929
0.8067	Intermediate Similarity	NPC73416
0.8067	Intermediate Similarity	NPC157133
0.8067	Intermediate Similarity	NPC160777
0.8056	Intermediate Similarity	NPC237330
0.8042	Intermediate Similarity	NPC153453
0.8041	Intermediate Similarity	NPC110419
0.8029	Intermediate Similarity	NPC194416
0.8029	Intermediate Similarity	NPC177291
0.8027	Intermediate Similarity	NPC474784
0.8026	Intermediate Similarity	NPC474903
0.8025	Intermediate Similarity	NPC153631
0.8014	Intermediate Similarity	NPC95679
0.8014	Intermediate Similarity	NPC112068
0.8014	Intermediate Similarity	NPC25305
0.8014	Intermediate Similarity	NPC226661
0.8014	Intermediate Similarity	NPC125417
0.8014	Intermediate Similarity	NPC278308
0.8014	Intermediate Similarity	NPC110899
0.8013	Intermediate Similarity	NPC165389
0.8	Intermediate Similarity	NPC142165
0.8	Intermediate Similarity	NPC276014
0.8	Intermediate Similarity	NPC105213
0.8	Intermediate Similarity	NPC305717
0.8	Intermediate Similarity	NPC274613
0.8	Intermediate Similarity	NPC196941
0.8	Intermediate Similarity	NPC309169
0.7987	Intermediate Similarity	NPC11314
0.7974	Intermediate Similarity	NPC237441
0.7974	Intermediate Similarity	NPC119669
0.7973	Intermediate Similarity	NPC326065
0.7971	Intermediate Similarity	NPC286573
0.7962	Intermediate Similarity	NPC158900
0.7947	Intermediate Similarity	NPC287495
0.7947	Intermediate Similarity	NPC225351
0.7947	Intermediate Similarity	NPC9370
0.7945	Intermediate Similarity	NPC90431
0.7943	Intermediate Similarity	NPC153990
0.7943	Intermediate Similarity	NPC158654
0.7933	Intermediate Similarity	NPC254659
0.7933	Intermediate Similarity	NPC287722
0.7931	Intermediate Similarity	NPC471110
0.7929	Intermediate Similarity	NPC473626
0.7929	Intermediate Similarity	NPC280767
0.7929	Intermediate Similarity	NPC3221
0.7922	Intermediate Similarity	NPC58661
0.7922	Intermediate Similarity	NPC472279
0.7914	Intermediate Similarity	NPC160900
0.7914	Intermediate Similarity	NPC140359
0.7914	Intermediate Similarity	NPC229084
0.7914	Intermediate Similarity	NPC106659
0.7914	Intermediate Similarity	NPC13020
0.7914	Intermediate Similarity	NPC18984
0.7908	Intermediate Similarity	NPC183655
0.7908	Intermediate Similarity	NPC287395
0.7905	Intermediate Similarity	NPC322021
0.7905	Intermediate Similarity	NPC66518
0.7902	Intermediate Similarity	NPC319282
0.7902	Intermediate Similarity	NPC244246
0.7902	Intermediate Similarity	NPC215941
0.7902	Intermediate Similarity	NPC275724
0.7902	Intermediate Similarity	NPC142985
0.7902	Intermediate Similarity	NPC137427
0.7902	Intermediate Similarity	NPC123196
0.7902	Intermediate Similarity	NPC65935
0.7902	Intermediate Similarity	NPC195292
0.7902	Intermediate Similarity	NPC311419
0.7881	Intermediate Similarity	NPC113397
0.7881	Intermediate Similarity	NPC275278
0.7877	Intermediate Similarity	NPC88065
0.7877	Intermediate Similarity	NPC95485
0.7877	Intermediate Similarity	NPC89504
0.7872	Intermediate Similarity	NPC154275
0.7871	Intermediate Similarity	NPC144283
0.7867	Intermediate Similarity	NPC299154
0.7862	Intermediate Similarity	NPC239855
0.7862	Intermediate Similarity	NPC475468
0.7857	Intermediate Similarity	NPC195763
0.7857	Intermediate Similarity	NPC142876
0.7857	Intermediate Similarity	NPC69430
0.7857	Intermediate Similarity	NPC200060
0.7857	Intermediate Similarity	NPC40290
0.7857	Intermediate Similarity	NPC92722
0.7857	Intermediate Similarity	NPC102003
0.7857	Intermediate Similarity	NPC333691
0.7857	Intermediate Similarity	NPC264550
0.7857	Intermediate Similarity	NPC264289
0.7857	Intermediate Similarity	NPC139293
0.7857	Intermediate Similarity	NPC205054
0.7847	Intermediate Similarity	NPC469480
0.7843	Intermediate Similarity	NPC52692
0.7843	Intermediate Similarity	NPC472969
0.7843	Intermediate Similarity	NPC125449
0.7843	Intermediate Similarity	NPC188074
0.7842	Intermediate Similarity	NPC139171
0.7832	Intermediate Similarity	NPC226855
0.7826	Intermediate Similarity	NPC109083
0.7826	Intermediate Similarity	NPC189844
0.7826	Intermediate Similarity	NPC224814
0.7826	Intermediate Similarity	NPC14007
0.7826	Intermediate Similarity	NPC269843
0.7826	Intermediate Similarity	NPC60962
0.7823	Intermediate Similarity	NPC471316
0.7821	Intermediate Similarity	NPC164912
0.7815	Intermediate Similarity	NPC119663
0.7815	Intermediate Similarity	NPC471417
0.7815	Intermediate Similarity	NPC473090
0.7808	Intermediate Similarity	NPC155098
0.7806	Intermediate Similarity	NPC29231
0.7806	Intermediate Similarity	NPC295977
0.7806	Intermediate Similarity	NPC58310
0.7794	Intermediate Similarity	NPC39793
0.7792	Intermediate Similarity	NPC254702
0.7792	Intermediate Similarity	NPC476394
0.7792	Intermediate Similarity	NPC194653
0.7792	Intermediate Similarity	NPC203747

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 NPC138438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	732
0.2-0.3	1230
0.3-0.4	2219
0.4-0.5	2322
0.5-0.6	1455
0.6-0.7	901
0.7-0.8	119
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8836	High Similarity	NPD824	Approved
0.8603	High Similarity	NPD9494	Approved
0.8182	Intermediate Similarity	NPD5977	Approved
0.8182	Intermediate Similarity	NPD5978	Approved
0.8105	Intermediate Similarity	NPD6386	Approved
0.8105	Intermediate Similarity	NPD6385	Approved
0.8042	Intermediate Similarity	NPD3142	Approved
0.8042	Intermediate Similarity	NPD3140	Approved
0.7914	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6873	Phase 2
0.7806	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD228	Approved
0.7725	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD2674	Phase 3
0.766	Intermediate Similarity	NPD1755	Approved
0.7628	Intermediate Similarity	NPD3455	Phase 2
0.7613	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5242	Approved
0.7595	Intermediate Similarity	NPD7577	Discontinued
0.7562	Intermediate Similarity	NPD3882	Suspended
0.755	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2801	Approved
0.7534	Intermediate Similarity	NPD3145	Approved
0.7534	Intermediate Similarity	NPD3144	Approved
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD1934	Approved
0.7468	Intermediate Similarity	NPD6876	Approved
0.7468	Intermediate Similarity	NPD6875	Approved
0.7421	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7110	Phase 1
0.741	Intermediate Similarity	NPD5536	Phase 2
0.7405	Intermediate Similarity	NPD2651	Approved
0.7405	Intermediate Similarity	NPD2649	Approved
0.74	Intermediate Similarity	NPD743	Approved
0.7397	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1670	Discontinued
0.7389	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3641	Approved
0.7389	Intermediate Similarity	NPD3640	Phase 3
0.7389	Intermediate Similarity	NPD3639	Approved
0.7386	Intermediate Similarity	NPD2654	Approved
0.7383	Intermediate Similarity	NPD447	Suspended
0.7376	Intermediate Similarity	NPD2667	Approved
0.7376	Intermediate Similarity	NPD2668	Approved
0.7375	Intermediate Similarity	NPD6844	Discontinued
0.7372	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3146	Approved
0.7349	Intermediate Similarity	NPD2898	Approved
0.7343	Intermediate Similarity	NPD3972	Approved
0.7343	Intermediate Similarity	NPD2233	Approved
0.7343	Intermediate Similarity	NPD2230	Approved
0.7343	Intermediate Similarity	NPD2232	Approved
0.7333	Intermediate Similarity	NPD2492	Phase 1
0.7329	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1240	Approved
0.7315	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD1511	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5718	Phase 2
0.7294	Intermediate Similarity	NPD7039	Approved
0.7294	Intermediate Similarity	NPD7038	Approved
0.7273	Intermediate Similarity	NPD3060	Approved
0.7262	Intermediate Similarity	NPD2163	Approved
0.7261	Intermediate Similarity	NPD4662	Approved
0.7261	Intermediate Similarity	NPD4661	Approved
0.7261	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD259	Phase 1
0.7246	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9545	Approved
0.7232	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD1607	Approved
0.7219	Intermediate Similarity	NPD2653	Approved
0.7215	Intermediate Similarity	NPD1512	Approved
0.72	Intermediate Similarity	NPD825	Approved
0.72	Intermediate Similarity	NPD826	Approved
0.719	Intermediate Similarity	NPD4476	Approved
0.719	Intermediate Similarity	NPD4477	Approved
0.719	Intermediate Similarity	NPD2935	Discontinued
0.7179	Intermediate Similarity	NPD5241	Discontinued
0.7171	Intermediate Similarity	NPD6895	Approved
0.7171	Intermediate Similarity	NPD6896	Approved
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2821	Approved
0.7161	Intermediate Similarity	NPD4236	Phase 3
0.7161	Intermediate Similarity	NPD4237	Approved
0.7161	Intermediate Similarity	NPD5177	Phase 3
0.716	Intermediate Similarity	NPD3818	Discontinued
0.7159	Intermediate Similarity	NPD2488	Approved
0.7159	Intermediate Similarity	NPD2490	Approved
0.7152	Intermediate Similarity	NPD555	Phase 2
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD257	Approved
0.7143	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD2491	Approved
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD258	Approved
0.7125	Intermediate Similarity	NPD3686	Approved
0.7125	Intermediate Similarity	NPD3687	Approved
0.7124	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1510	Phase 2
0.7124	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1241	Discontinued
0.7115	Intermediate Similarity	NPD4110	Phase 3
0.7115	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1445	Approved
0.7111	Intermediate Similarity	NPD1444	Approved
0.7103	Intermediate Similarity	NPD9269	Phase 2
0.7095	Intermediate Similarity	NPD9569	Approved
0.7089	Intermediate Similarity	NPD4357	Discontinued
0.7078	Intermediate Similarity	NPD2161	Phase 2
0.7078	Intermediate Similarity	NPD6032	Approved
0.7069	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6111	Discontinued
0.7059	Intermediate Similarity	NPD7177	Discontinued
0.7059	Intermediate Similarity	NPD2822	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6279	Approved
0.7055	Intermediate Similarity	NPD6280	Approved
0.7051	Intermediate Similarity	NPD4162	Approved
0.705	Intermediate Similarity	NPD9379	Approved
0.705	Intermediate Similarity	NPD9377	Approved
0.7049	Intermediate Similarity	NPD3057	Approved
0.7049	Intermediate Similarity	NPD3448	Approved
0.7048	Intermediate Similarity	NPD6862	Phase 2
0.7035	Intermediate Similarity	NPD3823	Discontinued
0.703	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6232	Discontinued
0.702	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1465	Phase 2
0.7007	Intermediate Similarity	NPD196	Phase 1
0.7007	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD2186	Approved
0.6993	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7074	Phase 3
0.6974	Remote Similarity	NPD2238	Phase 2
0.697	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3817	Phase 2
0.6968	Remote Similarity	NPD2240	Approved
0.6968	Remote Similarity	NPD2239	Approved
0.6966	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2309	Approved
0.6959	Remote Similarity	NPD3055	Approved
0.6959	Remote Similarity	NPD3053	Approved
0.6957	Remote Similarity	NPD2972	Approved
0.6957	Remote Similarity	NPD3533	Approved
0.6957	Remote Similarity	NPD1792	Phase 2
0.6954	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1651	Approved
0.6944	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1669	Approved
0.6939	Remote Similarity	NPD6582	Phase 2
0.6939	Remote Similarity	NPD6583	Phase 3
0.6933	Remote Similarity	NPD2614	Approved
0.6933	Remote Similarity	NPD4380	Phase 2
0.6923	Remote Similarity	NPD1375	Discontinued
0.6919	Remote Similarity	NPD7054	Approved
0.6918	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD9620	Approved
0.6913	Remote Similarity	NPD2798	Approved
0.6913	Remote Similarity	NPD9619	Approved
0.6913	Remote Similarity	NPD9621	Approved
0.6909	Remote Similarity	NPD2977	Approved
0.6909	Remote Similarity	NPD2978	Approved
0.6903	Remote Similarity	NPD2799	Discontinued
0.6902	Remote Similarity	NPD2494	Approved
0.6902	Remote Similarity	NPD2493	Approved
0.6899	Remote Similarity	NPD6331	Phase 2
0.6899	Remote Similarity	NPD8166	Discontinued
0.6893	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1283	Approved
0.6892	Remote Similarity	NPD5311	Approved
0.6892	Remote Similarity	NPD5310	Approved
0.689	Remote Similarity	NPD5090	Approved
0.689	Remote Similarity	NPD5089	Approved
0.6887	Remote Similarity	NPD9537	Phase 1
0.6887	Remote Similarity	NPD9536	Phase 1
0.6886	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7153	Discontinued
0.6879	Remote Similarity	NPD1549	Phase 2
0.6879	Remote Similarity	NPD2229	Approved
0.6879	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2234	Approved
0.6879	Remote Similarity	NPD2228	Approved
0.6879	Remote Similarity	NPD7472	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