NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	190.1
Volume:	206.03
LogP:	2.708
LogD:	2.729
LogS:	-2.964
# Rotatable Bonds:	1
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.557
Fsp3:	0.333
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:	-4.395
MDCK Permeability:	2.627015783218667e-05
Pgp-inhibitor:	0.236
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	90.71422576904297%
Volume Distribution (VD):	2.417
Pgp-substrate:	10.240714073181152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.854
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.359
CYP2C19-substrate:	0.727
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.773
CYP2D6-inhibitor:	0.864
CYP2D6-substrate:	0.794
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.533

ADMET: Excretion

Clearance (CL):	8.801
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.19
Skin Sensitization:	0.504
Carcinogencity:	0.816
Eye Corrosion:	0.004
Eye Irritation:	0.716
Respiratory Toxicity:	0.754

Download Data

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

Natural Product: NPC161696

Natural Product ID:	NPC161696
*Common Name:**	Eulatachromene
IUPAC Name:	(2,2-dimethylchromen-6-yl)methanol
Synonyms:	eulatachromene
Standard InCHIKey:	QNBPDVUHGIPLIS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O2/c1-12(2)6-5-10-7-9(8-13)3-4-11(10)14-12/h3-7,13H,8H2,1-2H3
SMILES:	OCc1ccc2c(c1)C=CC(O2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503271
PubChem CID:	14558470
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO21382	Eutypa lata	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608846]
NPO21382	Eutypa lata	Species	Diatrypaceae	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
Others	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT356	Organism	Vitis vinifera	Vitis vinifera	Activity	=	60.0	%	PMID[551396]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	GI	=	30.0	%	PMID[551397]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	100.0	%	PMID[551398]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	92.5	%	PMID[551398]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	40.0	%	PMID[551398]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	1.3	%	PMID[551398]

☑ 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 NPC161696 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	310
0.1-0.2	1661
0.2-0.3	4912
0.3-0.4	13331
0.4-0.5	4739
0.5-0.6	6005
0.6-0.7	8666
0.7-0.8	2809
0.8-0.85	214
0.85-0.9	46
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9151	High Similarity	NPC8302
0.9027	High Similarity	NPC142042
0.8962	High Similarity	NPC305205
0.8739	High Similarity	NPC106141
0.8729	High Similarity	NPC150026
0.8704	High Similarity	NPC38079
0.8704	High Similarity	NPC108875
0.8692	High Similarity	NPC51633
0.8678	High Similarity	NPC149796
0.8673	High Similarity	NPC90903
0.8667	High Similarity	NPC81641
0.8636	High Similarity	NPC251306
0.8624	High Similarity	NPC470393
0.8621	High Similarity	NPC74821
0.8611	High Similarity	NPC192596
0.8596	High Similarity	NPC235250
0.8595	High Similarity	NPC276212
0.8583	High Similarity	NPC197351
0.8583	High Similarity	NPC106914
0.8583	High Similarity	NPC246648
0.8583	High Similarity	NPC86502
0.8583	High Similarity	NPC134195
0.8583	High Similarity	NPC159132
0.8547	High Similarity	NPC295259
0.8537	High Similarity	NPC134360
0.8522	High Similarity	NPC473718
0.8512	High Similarity	NPC17809
0.8512	High Similarity	NPC285040
0.8512	High Similarity	NPC188022
0.8512	High Similarity	NPC102540
0.8512	High Similarity	NPC103420
0.8509	High Similarity	NPC301735
0.8505	High Similarity	NPC100870
0.8487	Intermediate Similarity	NPC212965
0.8475	Intermediate Similarity	NPC258979
0.8475	Intermediate Similarity	NPC8283
0.8475	Intermediate Similarity	NPC93398
0.8468	Intermediate Similarity	NPC194034
0.8462	Intermediate Similarity	NPC131118
0.8455	Intermediate Similarity	NPC274717
0.8448	Intermediate Similarity	NPC290470
0.8448	Intermediate Similarity	NPC154256
0.8421	Intermediate Similarity	NPC115379
0.8417	Intermediate Similarity	NPC120638
0.8417	Intermediate Similarity	NPC36016
0.8417	Intermediate Similarity	NPC100099
0.8407	Intermediate Similarity	NPC46844
0.8403	Intermediate Similarity	NPC473875
0.84	Intermediate Similarity	NPC293203
0.84	Intermediate Similarity	NPC118683
0.84	Intermediate Similarity	NPC211413
0.84	Intermediate Similarity	NPC164804
0.84	Intermediate Similarity	NPC244888
0.84	Intermediate Similarity	NPC68205
0.839	Intermediate Similarity	NPC32152
0.8376	Intermediate Similarity	NPC263754
0.8376	Intermediate Similarity	NPC183154
0.8361	Intermediate Similarity	NPC476254
0.8361	Intermediate Similarity	NPC131397
0.8361	Intermediate Similarity	NPC244495
0.8361	Intermediate Similarity	NPC93219
0.8348	Intermediate Similarity	NPC141003
0.8348	Intermediate Similarity	NPC35344
0.8347	Intermediate Similarity	NPC38761
0.8347	Intermediate Similarity	NPC76465
0.8333	Intermediate Similarity	NPC194277
0.8333	Intermediate Similarity	NPC54972
0.8333	Intermediate Similarity	NPC193364
0.8319	Intermediate Similarity	NPC232295
0.8319	Intermediate Similarity	NPC474131
0.8306	Intermediate Similarity	NPC38664
0.8306	Intermediate Similarity	NPC2401
0.8306	Intermediate Similarity	NPC185066
0.8306	Intermediate Similarity	NPC53986
0.8305	Intermediate Similarity	NPC283616
0.8291	Intermediate Similarity	NPC229147
0.8291	Intermediate Similarity	NPC85292
0.8291	Intermediate Similarity	NPC54507
0.8279	Intermediate Similarity	NPC270030
0.8268	Intermediate Similarity	NPC31849
0.8268	Intermediate Similarity	NPC77196
0.8268	Intermediate Similarity	NPC92805
0.8264	Intermediate Similarity	NPC74137
0.8261	Intermediate Similarity	NPC474920
0.8254	Intermediate Similarity	NPC103799
0.825	Intermediate Similarity	NPC475529
0.825	Intermediate Similarity	NPC218753
0.824	Intermediate Similarity	NPC93962
0.8235	Intermediate Similarity	NPC137294
0.8235	Intermediate Similarity	NPC85895
0.823	Intermediate Similarity	NPC291837
0.8226	Intermediate Similarity	NPC243688
0.8226	Intermediate Similarity	NPC224774
0.8226	Intermediate Similarity	NPC258567
0.8226	Intermediate Similarity	NPC121740
0.8214	Intermediate Similarity	NPC113457
0.8211	Intermediate Similarity	NPC470726
0.8211	Intermediate Similarity	NPC207179
0.8211	Intermediate Similarity	NPC167571
0.8211	Intermediate Similarity	NPC278552
0.8205	Intermediate Similarity	NPC185541
0.8205	Intermediate Similarity	NPC464
0.8203	Intermediate Similarity	NPC326600
0.8203	Intermediate Similarity	NPC97834
0.8203	Intermediate Similarity	NPC204353
0.8203	Intermediate Similarity	NPC115335
0.8203	Intermediate Similarity	NPC198154
0.8203	Intermediate Similarity	NPC296915
0.8203	Intermediate Similarity	NPC225696
0.8203	Intermediate Similarity	NPC62366
0.8203	Intermediate Similarity	NPC50896
0.8203	Intermediate Similarity	NPC223008
0.8197	Intermediate Similarity	NPC474160
0.8189	Intermediate Similarity	NPC13005
0.8182	Intermediate Similarity	NPC476633
0.8182	Intermediate Similarity	NPC52247
0.8175	Intermediate Similarity	NPC113098
0.8165	Intermediate Similarity	NPC128723
0.816	Intermediate Similarity	NPC222572
0.816	Intermediate Similarity	NPC87224
0.816	Intermediate Similarity	NPC469453
0.8158	Intermediate Similarity	NPC474272
0.8158	Intermediate Similarity	NPC306045
0.8158	Intermediate Similarity	NPC265211
0.8154	Intermediate Similarity	NPC294456
0.8154	Intermediate Similarity	NPC212124
0.8154	Intermediate Similarity	NPC184861
0.8154	Intermediate Similarity	NPC281014
0.8154	Intermediate Similarity	NPC225106
0.8145	Intermediate Similarity	NPC50315
0.8145	Intermediate Similarity	NPC283049
0.8145	Intermediate Similarity	NPC230479
0.8145	Intermediate Similarity	NPC470724
0.8145	Intermediate Similarity	NPC26879
0.8136	Intermediate Similarity	NPC69539
0.8136	Intermediate Similarity	NPC203113
0.8125	Intermediate Similarity	NPC163557
0.8125	Intermediate Similarity	NPC238115
0.8125	Intermediate Similarity	NPC85435
0.8125	Intermediate Similarity	NPC26394
0.8115	Intermediate Similarity	NPC248429
0.8115	Intermediate Similarity	NPC57199
0.8115	Intermediate Similarity	NPC46586
0.8115	Intermediate Similarity	NPC96286
0.8115	Intermediate Similarity	NPC204535
0.8115	Intermediate Similarity	NPC257188
0.8115	Intermediate Similarity	NPC13007
0.811	Intermediate Similarity	NPC268917
0.811	Intermediate Similarity	NPC129106
0.811	Intermediate Similarity	NPC118114
0.811	Intermediate Similarity	NPC196765
0.811	Intermediate Similarity	NPC207892
0.811	Intermediate Similarity	NPC129784
0.811	Intermediate Similarity	NPC17343
0.811	Intermediate Similarity	NPC280653
0.811	Intermediate Similarity	NPC236014
0.811	Intermediate Similarity	NPC12875
0.811	Intermediate Similarity	NPC476166
0.811	Intermediate Similarity	NPC206224
0.811	Intermediate Similarity	NPC272650
0.811	Intermediate Similarity	NPC29734
0.811	Intermediate Similarity	NPC300875
0.811	Intermediate Similarity	NPC228369
0.811	Intermediate Similarity	NPC267336
0.811	Intermediate Similarity	NPC164574
0.811	Intermediate Similarity	NPC150011
0.8103	Intermediate Similarity	NPC199462
0.8099	Intermediate Similarity	NPC269242
0.8099	Intermediate Similarity	NPC96423
0.8092	Intermediate Similarity	NPC151946
0.8092	Intermediate Similarity	NPC279573
0.8087	Intermediate Similarity	NPC88868
0.8087	Intermediate Similarity	NPC231251
0.8087	Intermediate Similarity	NPC25067
0.8083	Intermediate Similarity	NPC163036
0.8083	Intermediate Similarity	NPC172253
0.8083	Intermediate Similarity	NPC281356
0.8083	Intermediate Similarity	NPC59561
0.808	Intermediate Similarity	NPC46978
0.808	Intermediate Similarity	NPC469386
0.808	Intermediate Similarity	NPC473993
0.8077	Intermediate Similarity	NPC188380
0.8077	Intermediate Similarity	NPC38099
0.8077	Intermediate Similarity	NPC26954
0.8077	Intermediate Similarity	NPC262585
0.8077	Intermediate Similarity	NPC18189
0.8077	Intermediate Similarity	NPC20829
0.8077	Intermediate Similarity	NPC224543
0.8077	Intermediate Similarity	NPC78746
0.8073	Intermediate Similarity	NPC95755
0.807	Intermediate Similarity	NPC75440
0.807	Intermediate Similarity	NPC241549
0.8067	Intermediate Similarity	NPC238176
0.8067	Intermediate Similarity	NPC187993
0.8065	Intermediate Similarity	NPC293801
0.8065	Intermediate Similarity	NPC165556
0.8062	Intermediate Similarity	NPC224475
0.8062	Intermediate Similarity	NPC180716
0.8062	Intermediate Similarity	NPC124085
0.8062	Intermediate Similarity	NPC213173

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 NPC161696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	1034
0.2-0.3	1618
0.3-0.4	2688
0.4-0.5	1706
0.5-0.6	1041
0.6-0.7	624
0.7-0.8	144
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD1548	Phase 1
0.8468	Intermediate Similarity	NPD290	Approved
0.8393	Intermediate Similarity	NPD2684	Approved
0.8333	Intermediate Similarity	NPD1610	Phase 2
0.8214	Intermediate Similarity	NPD968	Approved
0.8182	Intermediate Similarity	NPD422	Phase 1
0.8175	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD8651	Approved
0.8103	Intermediate Similarity	NPD7843	Approved
0.8051	Intermediate Similarity	NPD6671	Approved
0.8033	Intermediate Similarity	NPD1091	Approved
0.8016	Intermediate Similarity	NPD4908	Phase 1
0.7984	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD5124	Phase 1
0.7949	Intermediate Similarity	NPD821	Approved
0.7937	Intermediate Similarity	NPD2861	Phase 2
0.7899	Intermediate Similarity	NPD7157	Approved
0.7891	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3691	Phase 2
0.7857	Intermediate Similarity	NPD3690	Phase 2
0.7812	Intermediate Similarity	NPD4625	Phase 3
0.7769	Intermediate Similarity	NPD1613	Approved
0.7769	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD4749	Approved
0.7724	Intermediate Similarity	NPD1778	Approved
0.7698	Intermediate Similarity	NPD6696	Suspended
0.7669	Intermediate Similarity	NPD7033	Discontinued
0.7652	Intermediate Similarity	NPD9697	Approved
0.7634	Intermediate Similarity	NPD4060	Phase 1
0.7619	Intermediate Similarity	NPD6582	Phase 2
0.7619	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6583	Phase 3
0.7615	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1241	Discontinued
0.7583	Intermediate Similarity	NPD594	Approved
0.7583	Intermediate Similarity	NPD592	Approved
0.7581	Intermediate Similarity	NPD6516	Phase 2
0.7581	Intermediate Similarity	NPD4626	Approved
0.7581	Intermediate Similarity	NPD5846	Approved
0.7578	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD228	Approved
0.7544	Intermediate Similarity	NPD846	Approved
0.7544	Intermediate Similarity	NPD940	Approved
0.7536	Intermediate Similarity	NPD6666	Approved
0.7536	Intermediate Similarity	NPD6667	Approved
0.7523	Intermediate Similarity	NPD9365	Approved
0.7519	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD5535	Approved
0.748	Intermediate Similarity	NPD3685	Discontinued
0.7463	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4538	Approved
0.7463	Intermediate Similarity	NPD4536	Approved
0.7459	Intermediate Similarity	NPD2557	Approved
0.7442	Intermediate Similarity	NPD6584	Phase 3
0.7438	Intermediate Similarity	NPD1398	Phase 1
0.7436	Intermediate Similarity	NPD3134	Approved
0.7422	Intermediate Similarity	NPD3225	Approved
0.7419	Intermediate Similarity	NPD1894	Discontinued
0.7411	Intermediate Similarity	NPD1809	Phase 2
0.7411	Intermediate Similarity	NPD2860	Approved
0.7411	Intermediate Similarity	NPD2859	Approved
0.7405	Intermediate Similarity	NPD3027	Phase 3
0.7402	Intermediate Similarity	NPD1608	Approved
0.7398	Intermediate Similarity	NPD3596	Phase 2
0.7395	Intermediate Similarity	NPD5451	Approved
0.7387	Intermediate Similarity	NPD845	Approved
0.7381	Intermediate Similarity	NPD3496	Discontinued
0.7373	Intermediate Similarity	NPD1358	Approved
0.7372	Intermediate Similarity	NPD2424	Discontinued
0.7364	Intermediate Similarity	NPD2797	Approved
0.7355	Intermediate Similarity	NPD1138	Approved
0.7348	Intermediate Similarity	NPD6798	Discontinued
0.7321	Intermediate Similarity	NPD2934	Approved
0.7321	Intermediate Similarity	NPD2933	Approved
0.7319	Intermediate Similarity	NPD1652	Phase 2
0.7313	Intermediate Similarity	NPD5735	Approved
0.7305	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2668	Approved
0.7302	Intermediate Similarity	NPD2667	Approved
0.7299	Intermediate Similarity	NPD6004	Phase 3
0.7299	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6002	Phase 3
0.7299	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6005	Phase 3
0.729	Intermediate Similarity	NPD111	Approved
0.7286	Intermediate Similarity	NPD5058	Phase 3
0.728	Intermediate Similarity	NPD1182	Approved
0.728	Intermediate Similarity	NPD6581	Approved
0.728	Intermediate Similarity	NPD6580	Approved
0.728	Intermediate Similarity	NPD9545	Approved
0.7279	Intermediate Similarity	NPD5960	Phase 3
0.7279	Intermediate Similarity	NPD5588	Approved
0.7273	Intermediate Similarity	NPD3180	Approved
0.7273	Intermediate Similarity	NPD1139	Approved
0.7273	Intermediate Similarity	NPD3179	Approved
0.7273	Intermediate Similarity	NPD1137	Approved
0.7266	Intermediate Similarity	NPD2235	Phase 2
0.7266	Intermediate Similarity	NPD2231	Phase 2
0.7259	Intermediate Similarity	NPD3052	Approved
0.7259	Intermediate Similarity	NPD3054	Approved
0.7259	Intermediate Similarity	NPD2157	Approved
0.7258	Intermediate Similarity	NPD7340	Approved
0.7246	Intermediate Similarity	NPD1549	Phase 2
0.7241	Intermediate Similarity	NPD291	Approved
0.7239	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD2238	Phase 2
0.7239	Intermediate Similarity	NPD4140	Approved
0.7234	Intermediate Similarity	NPD7213	Phase 3
0.7234	Intermediate Similarity	NPD7212	Phase 2
0.7226	Intermediate Similarity	NPD4476	Approved
0.7226	Intermediate Similarity	NPD4477	Approved
0.7222	Intermediate Similarity	NPD1357	Approved
0.7222	Intermediate Similarity	NPD3049	Approved
0.7222	Intermediate Similarity	NPD3443	Approved
0.7222	Intermediate Similarity	NPD3444	Approved
0.7222	Intermediate Similarity	NPD3445	Approved
0.7222	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD3020	Approved
0.7209	Intermediate Similarity	NPD5327	Phase 3
0.7206	Intermediate Similarity	NPD7097	Phase 1
0.7197	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1535	Discovery
0.7188	Intermediate Similarity	NPD1611	Approved
0.7185	Intermediate Similarity	NPD6355	Discontinued
0.7185	Intermediate Similarity	NPD4340	Discontinued
0.7183	Intermediate Similarity	NPD7447	Phase 1
0.7183	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD9295	Approved
0.7174	Intermediate Similarity	NPD5762	Approved
0.7174	Intermediate Similarity	NPD5763	Approved
0.7168	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD17	Approved
0.7154	Intermediate Similarity	NPD1283	Approved
0.7154	Intermediate Similarity	NPD5283	Phase 1
0.7153	Intermediate Similarity	NPD1510	Phase 2
0.7153	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7132	Intermediate Similarity	NPD2230	Approved
0.7132	Intermediate Similarity	NPD1481	Phase 2
0.7132	Intermediate Similarity	NPD1607	Approved
0.7132	Intermediate Similarity	NPD9717	Approved
0.7132	Intermediate Similarity	NPD2232	Approved
0.7132	Intermediate Similarity	NPD6353	Approved
0.7132	Intermediate Similarity	NPD2233	Approved
0.7123	Intermediate Similarity	NPD6072	Discontinued
0.7121	Intermediate Similarity	NPD4993	Discontinued
0.7121	Intermediate Similarity	NPD1712	Approved
0.7111	Intermediate Similarity	NPD1558	Phase 1
0.7109	Intermediate Similarity	NPD3847	Discontinued
0.7105	Intermediate Similarity	NPD844	Approved
0.7101	Intermediate Similarity	NPD2796	Approved
0.7099	Intermediate Similarity	NPD1818	Approved
0.7099	Intermediate Similarity	NPD1817	Approved
0.7099	Intermediate Similarity	NPD1794	Approved
0.7099	Intermediate Similarity	NPD1820	Approved
0.7099	Intermediate Similarity	NPD1819	Approved
0.7099	Intermediate Similarity	NPD987	Approved
0.709	Intermediate Similarity	NPD3268	Approved
0.709	Intermediate Similarity	NPD1296	Phase 2
0.7087	Intermediate Similarity	NPD1651	Approved
0.7077	Intermediate Similarity	NPD1669	Approved
0.7054	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD776	Approved
0.705	Intermediate Similarity	NPD7030	Discontinued
0.7045	Intermediate Similarity	NPD4624	Approved
0.7043	Intermediate Similarity	NPD288	Approved
0.7042	Intermediate Similarity	NPD6815	Approved
0.704	Intermediate Similarity	NPD6387	Discontinued
0.704	Intermediate Similarity	NPD709	Approved
0.7037	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7477	Discontinued
0.7031	Intermediate Similarity	NPD2554	Approved
0.7031	Intermediate Similarity	NPD2556	Approved
0.7029	Intermediate Similarity	NPD2799	Discontinued
0.7021	Intermediate Similarity	NPD3750	Approved
0.7015	Intermediate Similarity	NPD7095	Approved
0.7015	Intermediate Similarity	NPD5163	Phase 2
0.7015	Intermediate Similarity	NPD6179	Discontinued
0.7009	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1242	Phase 1
0.7007	Intermediate Similarity	NPD4097	Suspended
0.7007	Intermediate Similarity	NPD7411	Suspended
0.7007	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1840	Phase 2
0.6992	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3018	Phase 2
0.6985	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1551	Phase 2
0.6978	Remote Similarity	NPD6100	Approved
0.6978	Remote Similarity	NPD6099	Approved
0.6972	Remote Similarity	NPD2677	Approved
0.697	Remote Similarity	NPD1203	Approved
0.6967	Remote Similarity	NPD9380	Clinical (unspecified phase)

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