NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	196.11
Volume:	208.717
LogP:	1.664
LogD:	1.639
LogS:	-1.145
# Rotatable Bonds:	2
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	3.294
Fsp3:	0.455
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:	-4.705
MDCK Permeability:	8.456112482235767e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.515
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	83.0962142944336%
Volume Distribution (VD):	1.444
Pgp-substrate:	13.968012809753418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.695
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.457
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.326
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	14.425
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.794
Skin Sensitization:	0.75
Carcinogencity:	0.066
Eye Corrosion:	0.284
Eye Irritation:	0.946
Respiratory Toxicity:	0.433

Download Data

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

Natural Product: NPC473521

Natural Product ID:	NPC473521
*Common Name:**	Phenol A
IUPAC Name:	5-[(2S,3R)-3-hydroxybutan-2-yl]-4-methylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	ZYUVGYBAPZYKSA-HTRCEHHLSA-N
Standard InCHI:	InChI=1S/C11H16O3/c1-6(8(3)12)10-4-9(13)5-11(14)7(10)2/h4-6,8,12-14H,1-3H3/t6-,8-/m1/s1
SMILES:	CC1=C(C=C(C=C1O)O)C(C)C(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444472
PubChem CID:	11116966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO32513	Penicillium citrinum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18281952]
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[559422]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[559422]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[559422]
NPT1	Others	Radical scavenging activity		IC50	=	22500.0	nM	PMID[559421]

☑ 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 NPC473521 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	287
0.1-0.2	1481
0.2-0.3	4260
0.3-0.4	12838
0.4-0.5	6788
0.5-0.6	7418
0.6-0.7	7049
0.7-0.8	2279
0.8-0.85	202
0.85-0.9	84
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9174	High Similarity	NPC319803
0.9143	High Similarity	NPC471350
0.9074	High Similarity	NPC224870
0.9	High Similarity	NPC263753
0.8972	High Similarity	NPC61033
0.8972	High Similarity	NPC305603
0.8947	High Similarity	NPC3239
0.8919	High Similarity	NPC107240
0.8868	High Similarity	NPC244513
0.8868	High Similarity	NPC218879
0.8868	High Similarity	NPC227458
0.8807	High Similarity	NPC299568
0.8807	High Similarity	NPC186385
0.8807	High Similarity	NPC202647
0.8785	High Similarity	NPC37802
0.8783	High Similarity	NPC282255
0.8772	High Similarity	NPC9592
0.8772	High Similarity	NPC48781
0.8727	High Similarity	NPC475018
0.8704	High Similarity	NPC12640
0.8704	High Similarity	NPC248904
0.8704	High Similarity	NPC99836
0.8704	High Similarity	NPC201662
0.8679	High Similarity	NPC11280
0.8679	High Similarity	NPC137415
0.8679	High Similarity	NPC192032
0.8679	High Similarity	NPC294186
0.8679	High Similarity	NPC166313
0.8679	High Similarity	NPC24407
0.8679	High Similarity	NPC147310
0.8673	High Similarity	NPC474486
0.8667	High Similarity	NPC80027
0.8649	High Similarity	NPC225679
0.8649	High Similarity	NPC224527
0.8649	High Similarity	NPC165770
0.8649	High Similarity	NPC4493
0.8649	High Similarity	NPC476632
0.8624	High Similarity	NPC66834
0.8624	High Similarity	NPC232523
0.8624	High Similarity	NPC204901
0.8624	High Similarity	NPC158253
0.8621	High Similarity	NPC472071
0.8621	High Similarity	NPC223451
0.8609	High Similarity	NPC154030
0.8609	High Similarity	NPC471671
0.8598	High Similarity	NPC222522
0.8598	High Similarity	NPC313030
0.8598	High Similarity	NPC71002
0.8598	High Similarity	NPC94351
0.8598	High Similarity	NPC302219
0.8598	High Similarity	NPC249828
0.8598	High Similarity	NPC106396
0.8598	High Similarity	NPC53051
0.8598	High Similarity	NPC242342
0.8598	High Similarity	NPC146798
0.8598	High Similarity	NPC24404
0.8598	High Similarity	NPC85479
0.8598	High Similarity	NPC168303
0.8596	High Similarity	NPC115808
0.8585	High Similarity	NPC10588
0.8585	High Similarity	NPC166761
0.8571	High Similarity	NPC43525
0.8571	High Similarity	NPC166995
0.8559	High Similarity	NPC57199
0.8545	High Similarity	NPC174981
0.8534	High Similarity	NPC469644
0.8522	High Similarity	NPC172219
0.8522	High Similarity	NPC304510
0.8522	High Similarity	NPC470760
0.8519	High Similarity	NPC119860
0.8519	High Similarity	NPC30506
0.8519	High Similarity	NPC102216
0.8519	High Similarity	NPC475225
0.8509	High Similarity	NPC84999
0.8509	High Similarity	NPC246760
0.8505	High Similarity	NPC284011
0.8505	High Similarity	NPC72947
0.85	High Similarity	NPC293801
0.8496	Intermediate Similarity	NPC23804
0.8496	Intermediate Similarity	NPC117846
0.8496	Intermediate Similarity	NPC261343
0.8482	Intermediate Similarity	NPC151537
0.8468	Intermediate Similarity	NPC19808
0.8468	Intermediate Similarity	NPC33728
0.8448	Intermediate Similarity	NPC206
0.8448	Intermediate Similarity	NPC469609
0.844	Intermediate Similarity	NPC292452
0.844	Intermediate Similarity	NPC474839
0.8435	Intermediate Similarity	NPC308311
0.8435	Intermediate Similarity	NPC38893
0.8435	Intermediate Similarity	NPC477137
0.8426	Intermediate Similarity	NPC235762
0.8426	Intermediate Similarity	NPC471228
0.8407	Intermediate Similarity	NPC228425
0.8407	Intermediate Similarity	NPC302371
0.8396	Intermediate Similarity	NPC474073
0.8393	Intermediate Similarity	NPC132720
0.839	Intermediate Similarity	NPC102639
0.8381	Intermediate Similarity	NPC313650
0.8378	Intermediate Similarity	NPC63698
0.8378	Intermediate Similarity	NPC61885
0.8376	Intermediate Similarity	NPC151197
0.8376	Intermediate Similarity	NPC217174
0.8365	Intermediate Similarity	NPC295295
0.8364	Intermediate Similarity	NPC21594
0.8362	Intermediate Similarity	NPC477136
0.8349	Intermediate Similarity	NPC241891
0.8348	Intermediate Similarity	NPC472893
0.8348	Intermediate Similarity	NPC147179
0.8348	Intermediate Similarity	NPC192948
0.8348	Intermediate Similarity	NPC35797
0.8333	Intermediate Similarity	NPC100340
0.8333	Intermediate Similarity	NPC143659
0.8319	Intermediate Similarity	NPC39029
0.8319	Intermediate Similarity	NPC237667
0.8318	Intermediate Similarity	NPC128723
0.8305	Intermediate Similarity	NPC68339
0.8304	Intermediate Similarity	NPC473524
0.8293	Intermediate Similarity	NPC311293
0.8293	Intermediate Similarity	NPC148366
0.8288	Intermediate Similarity	NPC151477
0.8286	Intermediate Similarity	NPC245187
0.8276	Intermediate Similarity	NPC137496
0.8276	Intermediate Similarity	NPC308828
0.8276	Intermediate Similarity	NPC474358
0.8276	Intermediate Similarity	NPC219112
0.8276	Intermediate Similarity	NPC257540
0.8276	Intermediate Similarity	NPC474387
0.8276	Intermediate Similarity	NPC154511
0.8276	Intermediate Similarity	NPC247858
0.8273	Intermediate Similarity	NPC246056
0.8273	Intermediate Similarity	NPC134829
0.8264	Intermediate Similarity	NPC174729
0.8264	Intermediate Similarity	NPC139774
0.8261	Intermediate Similarity	NPC268160
0.8257	Intermediate Similarity	NPC168393
0.825	Intermediate Similarity	NPC120172
0.8246	Intermediate Similarity	NPC228452
0.8241	Intermediate Similarity	NPC211885
0.8241	Intermediate Similarity	NPC161571
0.8241	Intermediate Similarity	NPC275053
0.8241	Intermediate Similarity	NPC72729
0.8241	Intermediate Similarity	NPC130103
0.8241	Intermediate Similarity	NPC174911
0.8241	Intermediate Similarity	NPC248573
0.824	Intermediate Similarity	NPC238168
0.824	Intermediate Similarity	NPC237424
0.8235	Intermediate Similarity	NPC328504
0.823	Intermediate Similarity	NPC168657
0.8224	Intermediate Similarity	NPC77492
0.8224	Intermediate Similarity	NPC79241
0.8224	Intermediate Similarity	NPC6597
0.8205	Intermediate Similarity	NPC277588
0.8205	Intermediate Similarity	NPC320864
0.8198	Intermediate Similarity	NPC109691
0.8198	Intermediate Similarity	NPC470700
0.8198	Intermediate Similarity	NPC302681
0.8198	Intermediate Similarity	NPC39664
0.8198	Intermediate Similarity	NPC118286
0.8198	Intermediate Similarity	NPC39097
0.8197	Intermediate Similarity	NPC113495
0.8197	Intermediate Similarity	NPC105031
0.819	Intermediate Similarity	NPC325292
0.819	Intermediate Similarity	NPC808
0.819	Intermediate Similarity	NPC138117
0.8189	Intermediate Similarity	NPC474394
0.8182	Intermediate Similarity	NPC475580
0.8182	Intermediate Similarity	NPC53567
0.8158	Intermediate Similarity	NPC469912
0.8151	Intermediate Similarity	NPC69006
0.8142	Intermediate Similarity	NPC58865
0.8136	Intermediate Similarity	NPC144343
0.8131	Intermediate Similarity	NPC312132
0.8131	Intermediate Similarity	NPC259512
0.813	Intermediate Similarity	NPC91204
0.813	Intermediate Similarity	NPC82299
0.813	Intermediate Similarity	NPC170485
0.813	Intermediate Similarity	NPC237517
0.813	Intermediate Similarity	NPC111723
0.8125	Intermediate Similarity	NPC54844
0.812	Intermediate Similarity	NPC141090
0.812	Intermediate Similarity	NPC123559
0.812	Intermediate Similarity	NPC92
0.812	Intermediate Similarity	NPC469663
0.812	Intermediate Similarity	NPC150624
0.8115	Intermediate Similarity	NPC97578
0.8115	Intermediate Similarity	NPC228503
0.8115	Intermediate Similarity	NPC224342
0.8115	Intermediate Similarity	NPC138248
0.8108	Intermediate Similarity	NPC117115
0.8103	Intermediate Similarity	NPC249270
0.8103	Intermediate Similarity	NPC120280
0.8103	Intermediate Similarity	NPC473137
0.8103	Intermediate Similarity	NPC12656
0.8099	Intermediate Similarity	NPC74137
0.8099	Intermediate Similarity	NPC471794
0.8099	Intermediate Similarity	NPC71094
0.8095	Intermediate Similarity	NPC304541
0.808	Intermediate Similarity	NPC471519
0.808	Intermediate Similarity	NPC25729

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 NPC473521 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	941
0.2-0.3	1761
0.3-0.4	2979
0.4-0.5	1624
0.5-0.6	1078
0.6-0.7	401
0.7-0.8	64
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD940	Approved
0.8857	High Similarity	NPD846	Approved
0.8807	High Similarity	NPD4750	Phase 3
0.8241	Intermediate Similarity	NPD1242	Phase 1
0.8131	Intermediate Similarity	NPD288	Approved
0.8037	Intermediate Similarity	NPD844	Approved
0.7984	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD3091	Approved
0.7982	Intermediate Similarity	NPD3020	Approved
0.7944	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD1809	Phase 2
0.7869	Intermediate Similarity	NPD3092	Approved
0.7869	Intermediate Similarity	NPD1610	Phase 2
0.785	Intermediate Similarity	NPD845	Approved
0.776	Intermediate Similarity	NPD3094	Phase 2
0.7742	Intermediate Similarity	NPD4749	Approved
0.7734	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4908	Phase 1
0.7706	Intermediate Similarity	NPD2860	Approved
0.7706	Intermediate Similarity	NPD2859	Approved
0.7672	Intermediate Similarity	NPD3021	Approved
0.7672	Intermediate Similarity	NPD3022	Approved
0.7656	Intermediate Similarity	NPD3027	Phase 3
0.7627	Intermediate Similarity	NPD7635	Approved
0.7615	Intermediate Similarity	NPD2933	Approved
0.7615	Intermediate Similarity	NPD2934	Approved
0.7597	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3095	Discontinued
0.7541	Intermediate Similarity	NPD1548	Phase 1
0.7519	Intermediate Similarity	NPD4625	Phase 3
0.7481	Intermediate Similarity	NPD1613	Approved
0.7481	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD111	Approved
0.7422	Intermediate Similarity	NPD858	Approved
0.7422	Intermediate Similarity	NPD599	Approved
0.7422	Intermediate Similarity	NPD602	Approved
0.7422	Intermediate Similarity	NPD859	Approved
0.7417	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1444	Approved
0.7414	Intermediate Similarity	NPD1445	Approved
0.7395	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD1792	Phase 2
0.7364	Intermediate Similarity	NPD2861	Phase 2
0.735	Intermediate Similarity	NPD2342	Discontinued
0.7348	Intermediate Similarity	NPD2238	Phase 2
0.7344	Intermediate Similarity	NPD1134	Approved
0.7344	Intermediate Similarity	NPD1135	Approved
0.7344	Intermediate Similarity	NPD1131	Approved
0.7344	Intermediate Similarity	NPD1129	Approved
0.7344	Intermediate Similarity	NPD1133	Approved
0.728	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD4059	Approved
0.728	Intermediate Similarity	NPD3019	Approved
0.728	Intermediate Similarity	NPD4626	Approved
0.728	Intermediate Similarity	NPD2932	Approved
0.7259	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2568	Approved
0.7231	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5736	Approved
0.7226	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD9093	Approved
0.72	Intermediate Similarity	NPD4093	Discontinued
0.7177	Intermediate Similarity	NPD16	Approved
0.7177	Intermediate Similarity	NPD856	Approved
0.7176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD422	Phase 1
0.7165	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1751	Approved
0.7143	Intermediate Similarity	NPD9384	Approved
0.7143	Intermediate Similarity	NPD9089	Approved
0.7143	Intermediate Similarity	NPD9381	Approved
0.7131	Intermediate Similarity	NPD2228	Approved
0.7131	Intermediate Similarity	NPD2229	Approved
0.7131	Intermediate Similarity	NPD2234	Approved
0.7107	Intermediate Similarity	NPD228	Approved
0.709	Intermediate Similarity	NPD4060	Phase 1
0.709	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3620	Phase 2
0.708	Intermediate Similarity	NPD6100	Approved
0.708	Intermediate Similarity	NPD6099	Approved
0.7077	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9614	Approved
0.7073	Intermediate Similarity	NPD9618	Approved
0.7063	Intermediate Similarity	NPD5691	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.7054	Intermediate Similarity	NPD9622	Approved
0.7054	Intermediate Similarity	NPD4659	Approved
0.704	Intermediate Similarity	NPD317	Approved
0.704	Intermediate Similarity	NPD318	Approved
0.7031	Intermediate Similarity	NPD1201	Approved
0.7016	Intermediate Similarity	NPD6671	Approved
0.7015	Intermediate Similarity	NPD6405	Approved
0.7015	Intermediate Similarity	NPD6663	Approved
0.7015	Intermediate Similarity	NPD6407	Approved
0.7009	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6696	Suspended
0.7	Intermediate Similarity	NPD3892	Phase 2
0.7	Intermediate Similarity	NPD2684	Approved
0.6985	Remote Similarity	NPD4097	Suspended
0.6984	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7390	Discontinued
0.6963	Remote Similarity	NPD943	Approved
0.6957	Remote Similarity	NPD9273	Approved
0.6947	Remote Similarity	NPD4103	Phase 2
0.6947	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD37	Approved
0.6935	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5124	Phase 1
0.6912	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5735	Approved
0.6906	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD9615	Approved
0.6905	Remote Similarity	NPD9616	Approved
0.6905	Remote Similarity	NPD9613	Approved
0.6894	Remote Similarity	NPD9620	Approved
0.6894	Remote Similarity	NPD9619	Approved
0.6894	Remote Similarity	NPD9621	Approved
0.6884	Remote Similarity	NPD7742	Approved
0.6884	Remote Similarity	NPD7743	Approved
0.688	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD2286	Discontinued
0.6864	Remote Similarity	NPD9500	Approved
0.6855	Remote Similarity	NPD5283	Phase 1
0.685	Remote Similarity	NPD5304	Approved
0.685	Remote Similarity	NPD316	Approved
0.685	Remote Similarity	NPD5303	Approved
0.6846	Remote Similarity	NPD2233	Approved
0.6846	Remote Similarity	NPD2561	Approved
0.6846	Remote Similarity	NPD2562	Approved
0.6846	Remote Similarity	NPD2232	Approved
0.6846	Remote Similarity	NPD2230	Approved
0.6842	Remote Similarity	NPD3018	Phase 2
0.6842	Remote Similarity	NPD1712	Approved
0.6838	Remote Similarity	NPD1240	Approved
0.6838	Remote Similarity	NPD4140	Approved
0.6825	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1470	Approved
0.6815	Remote Similarity	NPD597	Approved
0.6815	Remote Similarity	NPD598	Approved
0.6815	Remote Similarity	NPD601	Approved
0.6815	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3552	Approved
0.6812	Remote Similarity	NPD3553	Approved
0.6812	Remote Similarity	NPD3554	Approved
0.6812	Remote Similarity	NPD3555	Approved
0.6807	Remote Similarity	NPD9610	Approved
0.6807	Remote Similarity	NPD9608	Approved
0.6806	Remote Similarity	NPD2532	Approved
0.6806	Remote Similarity	NPD2534	Approved
0.6806	Remote Similarity	NPD2533	Approved
0.68	Remote Similarity	NPD1791	Approved
0.68	Remote Similarity	NPD4965	Approved
0.68	Remote Similarity	NPD4967	Phase 2
0.68	Remote Similarity	NPD497	Approved
0.68	Remote Similarity	NPD1793	Approved
0.68	Remote Similarity	NPD4966	Approved
0.6797	Remote Similarity	NPD1357	Approved
0.6794	Remote Similarity	NPD5327	Phase 3
0.6791	Remote Similarity	NPD596	Approved
0.6791	Remote Similarity	NPD600	Approved
0.6788	Remote Similarity	NPD230	Phase 1
0.6786	Remote Similarity	NPD5762	Approved
0.6786	Remote Similarity	NPD5763	Approved
0.6774	Remote Similarity	NPD9377	Approved
0.6774	Remote Similarity	NPD9379	Approved
0.6774	Remote Similarity	NPD7843	Approved
0.6769	Remote Similarity	NPD3705	Approved
0.6769	Remote Similarity	NPD1091	Approved
0.6767	Remote Similarity	NPD2194	Approved
0.6767	Remote Similarity	NPD2195	Approved
0.6767	Remote Similarity	NPD4624	Approved
0.6765	Remote Similarity	NPD1132	Approved
0.6765	Remote Similarity	NPD1136	Approved
0.6765	Remote Similarity	NPD1130	Approved
0.6763	Remote Similarity	NPD1510	Phase 2
0.6761	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD9094	Approved
0.6748	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD709	Approved
0.6744	Remote Similarity	NPD4589	Approved
0.6742	Remote Similarity	NPD1283	Approved
0.6739	Remote Similarity	NPD2157	Approved
0.6739	Remote Similarity	NPD1607	Approved
0.6736	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7041	Phase 2
0.672	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1398	Phase 1
0.672	Remote Similarity	NPD496	Approved
0.672	Remote Similarity	NPD495	Approved
0.672	Remote Similarity	NPD498	Approved
0.6719	Remote Similarity	NPD7741	Discontinued
0.6718	Remote Similarity	NPD9269	Phase 2
0.6716	Remote Similarity	NPD3635	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