NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.08
Volume:	194.654
LogP:	1.88
LogD:	1.813
LogS:	-2.152
# Rotatable Bonds:	4
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	2.439
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.477
MDCK Permeability:	3.353935244376771e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.523
Plasma Protein Binding (PPB):	45.7294921875%
Volume Distribution (VD):	2.076
Pgp-substrate:	41.265708923339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.534
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.749
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.583
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.756
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	11.861
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.276
AMES Toxicity:	0.396
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.669
Skin Sensitization:	0.949
Carcinogencity:	0.895
Eye Corrosion:	0.008
Eye Irritation:	0.94
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC8302

Natural Product ID:	NPC8302
*Common Name:**	Terricollene C
IUPAC Name:	(4-buta-2,3-dienoxyphenyl)methanol
Synonyms:	Terricollene C
Standard InCHIKey:	LUYBTTHXSOULBZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12O2/c1-2-3-8-13-11-6-4-10(9-12)5-7-11/h3-7,12H,1,8-9H2
SMILES:	C=C=CCOc1ccc(cc1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL230162
PubChem CID:	44426063
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers

*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
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795843]
NPO1743	Neurospora terricola	Species	Sordariaceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	74450.0	nM	PMID[508004]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	85200.0	nM	PMID[508005]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	113600.0	nM	PMID[508005]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	76580.0	nM	PMID[508004]

☑ 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 NPC8302 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	297
0.1-0.2	1737
0.2-0.3	6088
0.3-0.4	13001
0.4-0.5	4345
0.5-0.6	7340
0.6-0.7	7580
0.7-0.8	2099
0.8-0.85	178
0.85-0.9	19
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC305205
0.93	High Similarity	NPC38079
0.93	High Similarity	NPC108875
0.9293	High Similarity	NPC51633
0.9238	High Similarity	NPC301735
0.9216	High Similarity	NPC251306
0.9208	High Similarity	NPC470393
0.92	High Similarity	NPC192596
0.9151	High Similarity	NPC235250
0.9151	High Similarity	NPC161696
0.9091	High Similarity	NPC100870
0.8962	High Similarity	NPC115379
0.8899	High Similarity	NPC142042
0.8774	High Similarity	NPC46844
0.8762	High Similarity	NPC291837
0.8667	High Similarity	NPC194034
0.8654	High Similarity	NPC238115
0.8649	High Similarity	NPC74821
0.8598	High Similarity	NPC88868
0.8598	High Similarity	NPC25067
0.8598	High Similarity	NPC231251
0.8584	High Similarity	NPC269242
0.8571	High Similarity	NPC300478
0.8571	High Similarity	NPC295259
0.8529	High Similarity	NPC471576
0.8519	High Similarity	NPC266932
0.8519	High Similarity	NPC55300
0.8496	Intermediate Similarity	NPC258979
0.8496	Intermediate Similarity	NPC8283
0.8496	Intermediate Similarity	NPC93398
0.8485	Intermediate Similarity	NPC321956
0.8482	Intermediate Similarity	NPC101503
0.8476	Intermediate Similarity	NPC473855
0.8469	Intermediate Similarity	NPC177844
0.8469	Intermediate Similarity	NPC99886
0.8469	Intermediate Similarity	NPC8002
0.8469	Intermediate Similarity	NPC259134
0.8468	Intermediate Similarity	NPC221049
0.844	Intermediate Similarity	NPC165646
0.8431	Intermediate Similarity	NPC95755
0.8426	Intermediate Similarity	NPC106141
0.8421	Intermediate Similarity	NPC469412
0.8421	Intermediate Similarity	NPC198734
0.8416	Intermediate Similarity	NPC313650
0.8396	Intermediate Similarity	NPC113457
0.8384	Intermediate Similarity	NPC71853
0.8384	Intermediate Similarity	NPC300017
0.8381	Intermediate Similarity	NPC474603
0.8381	Intermediate Similarity	NPC283546
0.8381	Intermediate Similarity	NPC12987
0.8367	Intermediate Similarity	NPC104216
0.8348	Intermediate Similarity	NPC193364
0.8348	Intermediate Similarity	NPC54972
0.8333	Intermediate Similarity	NPC60589
0.8333	Intermediate Similarity	NPC474272
0.8333	Intermediate Similarity	NPC265211
0.8333	Intermediate Similarity	NPC469708
0.8333	Intermediate Similarity	NPC306045
0.8319	Intermediate Similarity	NPC255675
0.8318	Intermediate Similarity	NPC227894
0.8302	Intermediate Similarity	NPC128730
0.8291	Intermediate Similarity	NPC109822
0.8291	Intermediate Similarity	NPC94276
0.8276	Intermediate Similarity	NPC71090
0.8276	Intermediate Similarity	NPC69403
0.8276	Intermediate Similarity	NPC36016
0.8276	Intermediate Similarity	NPC150026
0.8276	Intermediate Similarity	NPC100099
0.8276	Intermediate Similarity	NPC291189
0.8273	Intermediate Similarity	NPC153795
0.8273	Intermediate Similarity	NPC42911
0.8273	Intermediate Similarity	NPC280606
0.8273	Intermediate Similarity	NPC290353
0.8269	Intermediate Similarity	NPC107101
0.8261	Intermediate Similarity	NPC199023
0.8257	Intermediate Similarity	NPC137685
0.8246	Intermediate Similarity	NPC135961
0.8246	Intermediate Similarity	NPC181969
0.8246	Intermediate Similarity	NPC320987
0.8241	Intermediate Similarity	NPC241549
0.8241	Intermediate Similarity	NPC75440
0.8224	Intermediate Similarity	NPC176971
0.8224	Intermediate Similarity	NPC164576
0.8224	Intermediate Similarity	NPC473653
0.822	Intermediate Similarity	NPC194519
0.822	Intermediate Similarity	NPC207179
0.822	Intermediate Similarity	NPC167571
0.822	Intermediate Similarity	NPC81641
0.822	Intermediate Similarity	NPC278552
0.8218	Intermediate Similarity	NPC325292
0.8218	Intermediate Similarity	NPC138117
0.8214	Intermediate Similarity	NPC185541
0.8214	Intermediate Similarity	NPC301321
0.8214	Intermediate Similarity	NPC464
0.8208	Intermediate Similarity	NPC2518
0.8205	Intermediate Similarity	NPC76465
0.8205	Intermediate Similarity	NPC38761
0.82	Intermediate Similarity	NPC318429
0.819	Intermediate Similarity	NPC212965
0.819	Intermediate Similarity	NPC226712
0.819	Intermediate Similarity	NPC470804
0.819	Intermediate Similarity	NPC307425
0.8182	Intermediate Similarity	NPC78918
0.8182	Intermediate Similarity	NPC296920
0.8182	Intermediate Similarity	NPC139617
0.8182	Intermediate Similarity	NPC255068
0.8182	Intermediate Similarity	NPC90520
0.8174	Intermediate Similarity	NPC35071
0.8174	Intermediate Similarity	NPC177475
0.8174	Intermediate Similarity	NPC148615
0.8173	Intermediate Similarity	NPC171843
0.8151	Intermediate Similarity	NPC58607
0.8151	Intermediate Similarity	NPC191037
0.8151	Intermediate Similarity	NPC178284
0.8151	Intermediate Similarity	NPC276212
0.8148	Intermediate Similarity	NPC151530
0.8148	Intermediate Similarity	NPC258171
0.8148	Intermediate Similarity	NPC157473
0.8142	Intermediate Similarity	NPC154256
0.8142	Intermediate Similarity	NPC203113
0.8142	Intermediate Similarity	NPC229147
0.8142	Intermediate Similarity	NPC290470
0.8142	Intermediate Similarity	NPC141090
0.8142	Intermediate Similarity	NPC85292
0.8142	Intermediate Similarity	NPC54507
0.8137	Intermediate Similarity	NPC471581
0.8136	Intermediate Similarity	NPC106914
0.8136	Intermediate Similarity	NPC246648
0.8136	Intermediate Similarity	NPC221798
0.8136	Intermediate Similarity	NPC293701
0.8136	Intermediate Similarity	NPC197351
0.8136	Intermediate Similarity	NPC86502
0.8136	Intermediate Similarity	NPC48990
0.8136	Intermediate Similarity	NPC114901
0.8136	Intermediate Similarity	NPC134195
0.8125	Intermediate Similarity	NPC228287
0.8125	Intermediate Similarity	NPC180508
0.812	Intermediate Similarity	NPC120638
0.812	Intermediate Similarity	NPC209567
0.8113	Intermediate Similarity	NPC179686
0.8103	Intermediate Similarity	NPC473875
0.8103	Intermediate Similarity	NPC96423
0.8103	Intermediate Similarity	NPC475529
0.8095	Intermediate Similarity	NPC13755
0.8091	Intermediate Similarity	NPC168657
0.8091	Intermediate Similarity	NPC94045
0.8087	Intermediate Similarity	NPC163036
0.8083	Intermediate Similarity	NPC41706
0.8083	Intermediate Similarity	NPC121740
0.8083	Intermediate Similarity	NPC147821
0.8083	Intermediate Similarity	NPC224774
0.8083	Intermediate Similarity	NPC163332
0.8083	Intermediate Similarity	NPC292056
0.8083	Intermediate Similarity	NPC183181
0.8083	Intermediate Similarity	NPC319625
0.8083	Intermediate Similarity	NPC111247
0.8083	Intermediate Similarity	NPC118787
0.8083	Intermediate Similarity	NPC258567
0.8077	Intermediate Similarity	NPC175298
0.8073	Intermediate Similarity	NPC201959
0.807	Intermediate Similarity	NPC474933
0.807	Intermediate Similarity	NPC195466
0.8067	Intermediate Similarity	NPC102540
0.8067	Intermediate Similarity	NPC188022
0.8067	Intermediate Similarity	NPC17809
0.8067	Intermediate Similarity	NPC103420
0.8067	Intermediate Similarity	NPC285040
0.8056	Intermediate Similarity	NPC92623
0.8056	Intermediate Similarity	NPC135464
0.8036	Intermediate Similarity	NPC123175
0.8036	Intermediate Similarity	NPC176730
0.8034	Intermediate Similarity	NPC290451
0.8034	Intermediate Similarity	NPC97432
0.8034	Intermediate Similarity	NPC127389
0.8034	Intermediate Similarity	NPC190454
0.8034	Intermediate Similarity	NPC52247
0.8019	Intermediate Similarity	NPC300166
0.8018	Intermediate Similarity	NPC156840
0.8018	Intermediate Similarity	NPC257124
0.8018	Intermediate Similarity	NPC173746
0.8018	Intermediate Similarity	NPC8547
0.8017	Intermediate Similarity	NPC72529
0.8017	Intermediate Similarity	NPC247553
0.8017	Intermediate Similarity	NPC274717
0.8017	Intermediate Similarity	NPC229401
0.8017	Intermediate Similarity	NPC469453
0.8	Intermediate Similarity	NPC230479
0.8	Intermediate Similarity	NPC50315
0.8	Intermediate Similarity	NPC475236
0.8	Intermediate Similarity	NPC262573
0.8	Intermediate Similarity	NPC246358
0.8	Intermediate Similarity	NPC131118
0.8	Intermediate Similarity	NPC283616
0.8	Intermediate Similarity	NPC63083
0.8	Intermediate Similarity	NPC471215
0.8	Intermediate Similarity	NPC233731
0.8	Intermediate Similarity	NPC283049
0.8	Intermediate Similarity	NPC26879
0.8	Intermediate Similarity	NPC36108
0.8	Intermediate Similarity	NPC7097

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 NPC8302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	1000
0.2-0.3	1824
0.3-0.4	2569
0.4-0.5	1702
0.5-0.6	1011
0.6-0.7	610
0.7-0.8	130
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8762	High Similarity	NPD2684	Approved
0.875	High Similarity	NPD968	Approved
0.8667	High Similarity	NPD290	Approved
0.8649	High Similarity	NPD1548	Phase 1
0.844	Intermediate Similarity	NPD821	Approved
0.844	Intermediate Similarity	NPD7843	Approved
0.8348	Intermediate Similarity	NPD1610	Phase 2
0.8214	Intermediate Similarity	NPD7157	Approved
0.82	Intermediate Similarity	NPD9365	Approved
0.819	Intermediate Similarity	NPD1091	Approved
0.8034	Intermediate Similarity	NPD422	Phase 1
0.8018	Intermediate Similarity	NPD228	Approved
0.7934	Intermediate Similarity	NPD2861	Phase 2
0.789	Intermediate Similarity	NPD3134	Approved
0.7876	Intermediate Similarity	NPD1241	Discontinued
0.7869	Intermediate Similarity	NPD4908	Phase 1
0.7863	Intermediate Similarity	NPD1778	Approved
0.7863	Intermediate Similarity	NPD5846	Approved
0.7863	Intermediate Similarity	NPD6516	Phase 2
0.7845	Intermediate Similarity	NPD1894	Discontinued
0.7818	Intermediate Similarity	NPD1358	Approved
0.7778	Intermediate Similarity	NPD111	Approved
0.776	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD1613	Approved
0.775	Intermediate Similarity	NPD6583	Phase 3
0.775	Intermediate Similarity	NPD6582	Phase 2
0.775	Intermediate Similarity	NPD3685	Discontinued
0.7742	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6671	Approved
0.7692	Intermediate Similarity	NPD1182	Approved
0.7692	Intermediate Similarity	NPD9545	Approved
0.7686	Intermediate Similarity	NPD8651	Approved
0.7685	Intermediate Similarity	NPD291	Approved
0.7667	Intermediate Similarity	NPD2235	Phase 2
0.7667	Intermediate Similarity	NPD2231	Phase 2
0.7661	Intermediate Similarity	NPD3179	Approved
0.7661	Intermediate Similarity	NPD3180	Approved
0.7647	Intermediate Similarity	NPD9295	Approved
0.7636	Intermediate Similarity	NPD9697	Approved
0.7632	Intermediate Similarity	NPD5535	Approved
0.7627	Intermediate Similarity	NPD1357	Approved
0.7619	Intermediate Similarity	NPD2933	Approved
0.7619	Intermediate Similarity	NPD2934	Approved
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1535	Discovery
0.7581	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3691	Phase 2
0.7561	Intermediate Similarity	NPD6584	Phase 3
0.7561	Intermediate Similarity	NPD3690	Phase 2
0.7547	Intermediate Similarity	NPD2859	Approved
0.7547	Intermediate Similarity	NPD2860	Approved
0.7523	Intermediate Similarity	NPD940	Approved
0.7523	Intermediate Similarity	NPD846	Approved
0.7522	Intermediate Similarity	NPD5451	Approved
0.7522	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD3596	Phase 2
0.7521	Intermediate Similarity	NPD1608	Approved
0.7521	Intermediate Similarity	NPD1481	Phase 2
0.752	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3054	Approved
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD3052	Approved
0.748	Intermediate Similarity	NPD1820	Approved
0.748	Intermediate Similarity	NPD1819	Approved
0.748	Intermediate Similarity	NPD1818	Approved
0.748	Intermediate Similarity	NPD1817	Approved
0.746	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD4749	Approved
0.7453	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1242	Phase 1
0.7422	Intermediate Similarity	NPD4340	Discontinued
0.7398	Intermediate Similarity	NPD3225	Approved
0.7395	Intermediate Similarity	NPD6580	Approved
0.7395	Intermediate Similarity	NPD6581	Approved
0.7387	Intermediate Similarity	NPD9501	Approved
0.7377	Intermediate Similarity	NPD1840	Phase 2
0.736	Intermediate Similarity	NPD454	Approved
0.7345	Intermediate Similarity	NPD9552	Approved
0.7344	Intermediate Similarity	NPD1558	Phase 1
0.7339	Intermediate Similarity	NPD3020	Approved
0.7333	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD9294	Approved
0.7308	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4536	Approved
0.7308	Intermediate Similarity	NPD4538	Approved
0.7295	Intermediate Similarity	NPD3705	Approved
0.729	Intermediate Similarity	NPD9296	Approved
0.7288	Intermediate Similarity	NPD2557	Approved
0.7287	Intermediate Similarity	NPD5124	Phase 1
0.7287	Intermediate Similarity	NPD5735	Approved
0.7287	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD558	Phase 2
0.728	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2668	Approved
0.7273	Intermediate Similarity	NPD2667	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1423	Approved
0.7265	Intermediate Similarity	NPD5283	Phase 1
0.7265	Intermediate Similarity	NPD594	Approved
0.7265	Intermediate Similarity	NPD592	Approved
0.7258	Intermediate Similarity	NPD6696	Suspended
0.7252	Intermediate Similarity	NPD5588	Approved
0.7252	Intermediate Similarity	NPD7033	Discontinued
0.7252	Intermediate Similarity	NPD5960	Phase 3
0.7244	Intermediate Similarity	NPD3167	Approved
0.7244	Intermediate Similarity	NPD6179	Discontinued
0.7244	Intermediate Similarity	NPD4625	Phase 3
0.7244	Intermediate Similarity	NPD3165	Approved
0.7244	Intermediate Similarity	NPD3164	Approved
0.7244	Intermediate Similarity	NPD3166	Approved
0.7244	Intermediate Similarity	NPD5163	Phase 2
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7236	Intermediate Similarity	NPD9717	Approved
0.7222	Intermediate Similarity	NPD4993	Discontinued
0.7218	Intermediate Similarity	NPD1549	Phase 2
0.7213	Intermediate Similarity	NPD3847	Discontinued
0.7209	Intermediate Similarity	NPD4060	Phase 1
0.7209	Intermediate Similarity	NPD4140	Approved
0.72	Intermediate Similarity	NPD1794	Approved
0.72	Intermediate Similarity	NPD3568	Approved
0.72	Intermediate Similarity	NPD987	Approved
0.72	Intermediate Similarity	NPD3567	Approved
0.719	Intermediate Similarity	NPD6382	Discontinued
0.719	Intermediate Similarity	NPD5585	Approved
0.719	Intermediate Similarity	NPD5691	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5327	Phase 3
0.7177	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD682	Discontinued
0.7164	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD1652	Phase 2
0.7132	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6667	Approved
0.7132	Intermediate Similarity	NPD6666	Approved
0.7132	Intermediate Similarity	NPD6233	Phase 2
0.7132	Intermediate Similarity	NPD4062	Phase 3
0.7087	Intermediate Similarity	NPD1712	Approved
0.7077	Intermediate Similarity	NPD2238	Phase 2
0.7077	Intermediate Similarity	NPD1240	Approved
0.7077	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD556	Approved
0.7068	Intermediate Similarity	NPD1551	Phase 2
0.7064	Intermediate Similarity	NPD844	Approved
0.7064	Intermediate Similarity	NPD1809	Phase 2
0.7063	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD6362	Approved
0.7063	Intermediate Similarity	NPD1203	Approved
0.7054	Intermediate Similarity	NPD1048	Approved
0.7049	Intermediate Similarity	NPD3444	Approved
0.7049	Intermediate Similarity	NPD3443	Approved
0.7049	Intermediate Similarity	NPD3049	Approved
0.7049	Intermediate Similarity	NPD3445	Approved
0.704	Intermediate Similarity	NPD6540	Phase 3
0.704	Intermediate Similarity	NPD2982	Phase 2
0.704	Intermediate Similarity	NPD6543	Approved
0.704	Intermediate Similarity	NPD2428	Approved
0.704	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6542	Approved
0.704	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6539	Approved
0.704	Intermediate Similarity	NPD2429	Approved
0.704	Intermediate Similarity	NPD2983	Phase 2
0.704	Intermediate Similarity	NPD4129	Approved
0.7037	Intermediate Similarity	NPD845	Approved
0.7034	Intermediate Similarity	NPD1138	Approved
0.7031	Intermediate Similarity	NPD2614	Approved
0.7031	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD317	Approved
0.7025	Intermediate Similarity	NPD856	Approved
0.7025	Intermediate Similarity	NPD16	Approved
0.7025	Intermediate Similarity	NPD318	Approved
0.7023	Intermediate Similarity	NPD6355	Discontinued
0.7016	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD776	Approved
0.7015	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1375	Discontinued
0.7015	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6004	Phase 3
0.7015	Intermediate Similarity	NPD6005	Phase 3
0.7015	Intermediate Similarity	NPD6002	Phase 3
0.7008	Intermediate Similarity	NPD5647	Approved
0.7007	Intermediate Similarity	NPD5058	Phase 3
0.7007	Intermediate Similarity	NPD6815	Approved
0.7	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD709	Approved
0.7	Intermediate Similarity	NPD288	Approved
0.7	Intermediate Similarity	NPD5745	Approved
0.6992	Remote Similarity	NPD1510	Phase 2
0.6992	Remote Similarity	NPD2554	Approved
0.6992	Remote Similarity	NPD2556	Approved
0.6984	Remote Similarity	NPD6538	Approved
0.6984	Remote Similarity	NPD6541	Approved
0.6984	Remote Similarity	NPD1283	Approved
0.6984	Remote Similarity	NPD196	Phase 1

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