NPASS Compound

Structure

NPC473934 OpenBabel07101719512D 26 28 0 0 0 0 0 0 0 0999 V2000 -5.2682 -3.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7077 -3.9011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1072 1.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 0.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 -0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8399 -2.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8371 -2.1739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 -1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 0.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2710 -3.0749 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1044 1.5047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 -2.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 -0.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.18
Volume:	373.805
LogP:	4.192
LogD:	3.336
LogS:	-4.692
# Rotatable Bonds:	6
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	2.675
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.758
MDCK Permeability:	2.3754702851874754e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.707

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	91.3149642944336%
Volume Distribution (VD):	2.772
Pgp-substrate:	6.708340167999268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.718
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.971
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.966
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	9.211
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.468
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.208
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.38
Skin Sensitization:	0.951
Carcinogencity:	0.148
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC473934

Natural Product ID:	NPC473934
*Common Name:**	Secocularine
IUPAC Name:	N,N-dimethyl-2-(2,3,10-trimethoxybenzo[b][1]benzoxepin-7-yl)ethanamine
Synonyms:	Secocularine
Standard InCHIKey:	ZIEYKOGDJZHQIE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H25NO4/c1-22(2)11-10-14-7-9-17(23-3)21-16(14)8-6-15-12-19(24-4)20(25-5)13-18(15)26-21/h6-9,12-13H,10-11H2,1-5H3
SMILES:	CN(C)CCC1=C2C=CC3=CC(=C(C=C3OC2=C(C=C1)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455632
PubChem CID:	21771742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001910] Benzoxepines [CHEMONTID:0001988] Dibenzoxepines

*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
NPO32444	sarcuajmos saetavensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8676127]

☑ 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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	=	28200.0	nM	PMID[543311]
NPT2	Others	Unspecified		Ratio IC50	>	3.5	n.a.	PMID[543311]
NPT2	Others	Unspecified		Ratio IC50	=	0.8	n.a.	PMID[543311]

☑ 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 NPC473934 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	333
0.1-0.2	1717
0.2-0.3	8291
0.3-0.4	10802
0.4-0.5	4439
0.5-0.6	7442
0.6-0.7	7423
0.7-0.8	2139
0.8-0.85	105
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9514	High Similarity	NPC475557
0.8553	High Similarity	NPC190783
0.8553	High Similarity	NPC232386
0.8553	High Similarity	NPC152680
0.8421	Intermediate Similarity	NPC114124
0.8365	Intermediate Similarity	NPC204908
0.8365	Intermediate Similarity	NPC83198
0.8333	Intermediate Similarity	NPC293093
0.8248	Intermediate Similarity	NPC472596
0.8239	Intermediate Similarity	NPC262641
0.8207	Intermediate Similarity	NPC474478
0.8205	Intermediate Similarity	NPC129603
0.8169	Intermediate Similarity	NPC31707
0.8148	Intermediate Similarity	NPC10908
0.8148	Intermediate Similarity	NPC227060
0.8148	Intermediate Similarity	NPC198498
0.8148	Intermediate Similarity	NPC317439
0.8148	Intermediate Similarity	NPC317145
0.8148	Intermediate Similarity	NPC276890
0.8148	Intermediate Similarity	NPC76682
0.8148	Intermediate Similarity	NPC115284
0.8148	Intermediate Similarity	NPC63646
0.8129	Intermediate Similarity	NPC194626
0.8129	Intermediate Similarity	NPC261661
0.8117	Intermediate Similarity	NPC218575
0.8105	Intermediate Similarity	NPC211296
0.8102	Intermediate Similarity	NPC308217
0.8099	Intermediate Similarity	NPC189248
0.8099	Intermediate Similarity	NPC202904
0.8098	Intermediate Similarity	NPC12424
0.8098	Intermediate Similarity	NPC41376
0.8098	Intermediate Similarity	NPC251580
0.8098	Intermediate Similarity	NPC129518
0.8095	Intermediate Similarity	NPC173660
0.8082	Intermediate Similarity	NPC474600
0.8069	Intermediate Similarity	NPC475856
0.8056	Intermediate Similarity	NPC224157
0.8056	Intermediate Similarity	NPC214860
0.8056	Intermediate Similarity	NPC192687
0.8056	Intermediate Similarity	NPC476399
0.8056	Intermediate Similarity	NPC237169
0.8056	Intermediate Similarity	NPC470624
0.8056	Intermediate Similarity	NPC229231
0.8042	Intermediate Similarity	NPC207702
0.8042	Intermediate Similarity	NPC149008
0.8042	Intermediate Similarity	NPC283114
0.8039	Intermediate Similarity	NPC59907
0.8039	Intermediate Similarity	NPC37144
0.8039	Intermediate Similarity	NPC178129
0.8028	Intermediate Similarity	NPC244364
0.8027	Intermediate Similarity	NPC195022
0.8027	Intermediate Similarity	NPC472337
0.8014	Intermediate Similarity	NPC94236
0.8014	Intermediate Similarity	NPC37196
0.8014	Intermediate Similarity	NPC105513
0.8014	Intermediate Similarity	NPC269528
0.8012	Intermediate Similarity	NPC13916
0.8012	Intermediate Similarity	NPC264850
0.8	Intermediate Similarity	NPC264885
0.8	Intermediate Similarity	NPC141493
0.8	Intermediate Similarity	NPC184928
0.7988	Intermediate Similarity	NPC212237
0.7988	Intermediate Similarity	NPC116465
0.7987	Intermediate Similarity	NPC471388
0.7987	Intermediate Similarity	NPC25966
0.7987	Intermediate Similarity	NPC245207
0.7987	Intermediate Similarity	NPC127218
0.7987	Intermediate Similarity	NPC319647
0.7986	Intermediate Similarity	NPC45824
0.7986	Intermediate Similarity	NPC190144
0.7986	Intermediate Similarity	NPC474227
0.7986	Intermediate Similarity	NPC10225
0.7986	Intermediate Similarity	NPC58164
0.7975	Intermediate Similarity	NPC148014
0.7975	Intermediate Similarity	NPC78359
0.7975	Intermediate Similarity	NPC40389
0.7975	Intermediate Similarity	NPC65490
0.7975	Intermediate Similarity	NPC315707
0.7973	Intermediate Similarity	NPC205442
0.7973	Intermediate Similarity	NPC472336
0.7973	Intermediate Similarity	NPC472334
0.7973	Intermediate Similarity	NPC286843
0.7972	Intermediate Similarity	NPC471986
0.7972	Intermediate Similarity	NPC172403
0.7971	Intermediate Similarity	NPC475961
0.7971	Intermediate Similarity	NPC254625
0.7961	Intermediate Similarity	NPC50250
0.7956	Intermediate Similarity	NPC304208
0.7956	Intermediate Similarity	NPC52464
0.795	Intermediate Similarity	NPC24465
0.795	Intermediate Similarity	NPC180306
0.7945	Intermediate Similarity	NPC161203
0.7945	Intermediate Similarity	NPC6451
0.7933	Intermediate Similarity	NPC27495
0.7933	Intermediate Similarity	NPC254759
0.7933	Intermediate Similarity	NPC213206
0.7933	Intermediate Similarity	NPC474915
0.7933	Intermediate Similarity	NPC328750
0.7933	Intermediate Similarity	NPC188163
0.7933	Intermediate Similarity	NPC160283
0.7931	Intermediate Similarity	NPC234488
0.7931	Intermediate Similarity	NPC299221
0.7931	Intermediate Similarity	NPC51840
0.7931	Intermediate Similarity	NPC126836
0.7931	Intermediate Similarity	NPC311680
0.7929	Intermediate Similarity	NPC477886
0.7925	Intermediate Similarity	NPC329837
0.7919	Intermediate Similarity	NPC326797
0.7919	Intermediate Similarity	NPC107551
0.7919	Intermediate Similarity	NPC296898
0.7919	Intermediate Similarity	NPC103976
0.7919	Intermediate Similarity	NPC102904
0.7919	Intermediate Similarity	NPC276490
0.7919	Intermediate Similarity	NPC176051
0.7919	Intermediate Similarity	NPC474282
0.7917	Intermediate Similarity	NPC210674
0.7917	Intermediate Similarity	NPC474623
0.7917	Intermediate Similarity	NPC474651
0.7917	Intermediate Similarity	NPC63179
0.7911	Intermediate Similarity	NPC180756
0.7911	Intermediate Similarity	NPC323443
0.7905	Intermediate Similarity	NPC42793
0.7905	Intermediate Similarity	NPC234865
0.7905	Intermediate Similarity	NPC167944
0.7905	Intermediate Similarity	NPC231884
0.7905	Intermediate Similarity	NPC201357
0.7905	Intermediate Similarity	NPC281521
0.7905	Intermediate Similarity	NPC255147
0.7904	Intermediate Similarity	NPC243454
0.7904	Intermediate Similarity	NPC475479
0.7902	Intermediate Similarity	NPC112571
0.7902	Intermediate Similarity	NPC285725
0.7902	Intermediate Similarity	NPC50683
0.7899	Intermediate Similarity	NPC474612
0.7895	Intermediate Similarity	NPC6568
0.7895	Intermediate Similarity	NPC258083
0.7891	Intermediate Similarity	NPC168059
0.7891	Intermediate Similarity	NPC263064
0.7891	Intermediate Similarity	NPC229442
0.7891	Intermediate Similarity	NPC32778
0.7883	Intermediate Similarity	NPC123948
0.7882	Intermediate Similarity	NPC14507
0.7882	Intermediate Similarity	NPC47077
0.7881	Intermediate Similarity	NPC471389
0.7879	Intermediate Similarity	NPC228040
0.7877	Intermediate Similarity	NPC474238
0.7877	Intermediate Similarity	NPC232275
0.7877	Intermediate Similarity	NPC474356
0.7877	Intermediate Similarity	NPC149337
0.7877	Intermediate Similarity	NPC12275
0.7877	Intermediate Similarity	NPC45715
0.7877	Intermediate Similarity	NPC471983
0.7867	Intermediate Similarity	NPC79622
0.7867	Intermediate Similarity	NPC292882
0.7867	Intermediate Similarity	NPC314682
0.7867	Intermediate Similarity	NPC212942
0.7867	Intermediate Similarity	NPC29868
0.7862	Intermediate Similarity	NPC285339
0.7862	Intermediate Similarity	NPC218856
0.7862	Intermediate Similarity	NPC476572
0.7862	Intermediate Similarity	NPC3439
0.7862	Intermediate Similarity	NPC202582
0.7862	Intermediate Similarity	NPC273295
0.7862	Intermediate Similarity	NPC210623
0.7862	Intermediate Similarity	NPC470258
0.7862	Intermediate Similarity	NPC190629
0.7862	Intermediate Similarity	NPC222004
0.7862	Intermediate Similarity	NPC160193
0.7862	Intermediate Similarity	NPC226788
0.7857	Intermediate Similarity	NPC112251
0.7857	Intermediate Similarity	NPC239584
0.7857	Intermediate Similarity	NPC16107
0.7857	Intermediate Similarity	NPC210437
0.7857	Intermediate Similarity	NPC476144
0.7857	Intermediate Similarity	NPC286119
0.7857	Intermediate Similarity	NPC195538
0.7857	Intermediate Similarity	NPC51957
0.7857	Intermediate Similarity	NPC106295
0.7852	Intermediate Similarity	NPC78047
0.7852	Intermediate Similarity	NPC476698
0.7852	Intermediate Similarity	NPC265433
0.7852	Intermediate Similarity	NPC234952
0.7852	Intermediate Similarity	NPC162659
0.7852	Intermediate Similarity	NPC248727
0.7852	Intermediate Similarity	NPC270456
0.7847	Intermediate Similarity	NPC216836
0.7847	Intermediate Similarity	NPC291847
0.7847	Intermediate Similarity	NPC474119
0.7847	Intermediate Similarity	NPC210355
0.7847	Intermediate Similarity	NPC474670
0.7847	Intermediate Similarity	NPC242032
0.7843	Intermediate Similarity	NPC145304
0.7842	Intermediate Similarity	NPC15805
0.7838	Intermediate Similarity	NPC310854
0.7838	Intermediate Similarity	NPC11147
0.7838	Intermediate Similarity	NPC106215
0.7832	Intermediate Similarity	NPC105925
0.7832	Intermediate Similarity	NPC64391
0.7829	Intermediate Similarity	NPC472562
0.7829	Intermediate Similarity	NPC80326

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 NPC473934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	893
0.2-0.3	1334
0.3-0.4	2501
0.4-0.5	2120
0.5-0.6	1207
0.6-0.7	669
0.7-0.8	194
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8446	Intermediate Similarity	NPD7124	Phase 2
0.8429	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD8251	Approved
0.8148	Intermediate Similarity	NPD8252	Approved
0.8148	Intermediate Similarity	NPD8099	Discontinued
0.8098	Intermediate Similarity	NPD8156	Discontinued
0.8065	Intermediate Similarity	NPD4675	Approved
0.8065	Intermediate Similarity	NPD4678	Approved
0.8	Intermediate Similarity	NPD5677	Discontinued
0.7975	Intermediate Similarity	NPD2563	Approved
0.7975	Intermediate Similarity	NPD2560	Approved
0.7933	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5718	Phase 2
0.7905	Intermediate Similarity	NPD6111	Discontinued
0.7905	Intermediate Similarity	NPD6896	Approved
0.7905	Intermediate Similarity	NPD6895	Approved
0.7885	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4055	Discovery
0.7862	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4584	Approved
0.7857	Intermediate Similarity	NPD1424	Approved
0.7812	Intermediate Similarity	NPD6788	Approved
0.7811	Intermediate Similarity	NPD8053	Approved
0.7811	Intermediate Similarity	NPD8054	Approved
0.7806	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4585	Approved
0.7778	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4005	Discontinued
0.7763	Intermediate Similarity	NPD4162	Approved
0.7756	Intermediate Similarity	NPD6030	Approved
0.7756	Intermediate Similarity	NPD6031	Approved
0.7742	Intermediate Similarity	NPD4123	Phase 3
0.7714	Intermediate Similarity	NPD3443	Approved
0.7714	Intermediate Similarity	NPD3445	Approved
0.7714	Intermediate Similarity	NPD3444	Approved
0.7712	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2238	Phase 2
0.7692	Intermediate Similarity	NPD7549	Discontinued
0.7683	Intermediate Similarity	NPD6071	Discontinued
0.7662	Intermediate Similarity	NPD5241	Discontinued
0.7647	Intermediate Similarity	NPD3060	Approved
0.7643	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1375	Discontinued
0.7625	Intermediate Similarity	NPD3382	Approved
0.7625	Intermediate Similarity	NPD3384	Approved
0.7625	Intermediate Similarity	NPD3383	Approved
0.7603	Intermediate Similarity	NPD3018	Phase 2
0.76	Intermediate Similarity	NPD2653	Approved
0.7597	Intermediate Similarity	NPD7466	Approved
0.7595	Intermediate Similarity	NPD4210	Discontinued
0.759	Intermediate Similarity	NPD4481	Phase 3
0.7586	Intermediate Similarity	NPD4098	Discontinued
0.758	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3051	Approved
0.7562	Intermediate Similarity	NPD5089	Approved
0.7562	Intermediate Similarity	NPD5090	Approved
0.7551	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2200	Suspended
0.7548	Intermediate Similarity	NPD2677	Approved
0.7546	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5177	Phase 3
0.7532	Intermediate Similarity	NPD4236	Phase 3
0.7532	Intermediate Similarity	NPD4237	Approved
0.753	Intermediate Similarity	NPD2969	Approved
0.753	Intermediate Similarity	NPD2970	Approved
0.7517	Intermediate Similarity	NPD4474	Approved
0.7517	Intermediate Similarity	NPD4475	Approved
0.7516	Intermediate Similarity	NPD7447	Phase 1
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7484	Intermediate Similarity	NPD3686	Approved
0.7484	Intermediate Similarity	NPD3687	Approved
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3294	Phase 2
0.7471	Intermediate Similarity	NPD7906	Approved
0.7468	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1613	Approved
0.7453	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7110	Phase 1
0.7452	Intermediate Similarity	NPD7213	Phase 3
0.7452	Intermediate Similarity	NPD7212	Phase 2
0.745	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2982	Phase 2
0.7448	Intermediate Similarity	NPD2983	Phase 2
0.744	Intermediate Similarity	NPD3489	Phase 3
0.7425	Intermediate Similarity	NPD5242	Approved
0.7421	Intermediate Similarity	NPD5976	Discontinued
0.7414	Intermediate Similarity	NPD4663	Approved
0.741	Intermediate Similarity	NPD5283	Phase 1
0.7394	Intermediate Similarity	NPD2486	Discontinued
0.7391	Intermediate Similarity	NPD6876	Approved
0.7391	Intermediate Similarity	NPD6875	Approved
0.7381	Intermediate Similarity	NPD2489	Approved
0.7381	Intermediate Similarity	NPD27	Approved
0.7379	Intermediate Similarity	NPD2230	Approved
0.7379	Intermediate Similarity	NPD2232	Approved
0.7379	Intermediate Similarity	NPD2233	Approved
0.7372	Intermediate Similarity	NPD6331	Phase 2
0.7362	Intermediate Similarity	NPD5773	Approved
0.7362	Intermediate Similarity	NPD5772	Approved
0.7355	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6072	Discontinued
0.7346	Intermediate Similarity	NPD6385	Approved
0.7346	Intermediate Similarity	NPD6386	Approved
0.7343	Intermediate Similarity	NPD6382	Discontinued
0.7342	Intermediate Similarity	NPD5297	Approved
0.7342	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7311	Approved
0.7341	Intermediate Similarity	NPD7310	Approved
0.7341	Intermediate Similarity	NPD7313	Approved
0.7341	Intermediate Similarity	NPD4578	Approved
0.7341	Intermediate Similarity	NPD4577	Approved
0.7341	Intermediate Similarity	NPD7312	Approved
0.7333	Intermediate Similarity	NPD7833	Phase 2
0.7333	Intermediate Similarity	NPD5109	Approved
0.7333	Intermediate Similarity	NPD5111	Phase 2
0.7333	Intermediate Similarity	NPD7831	Phase 2
0.7333	Intermediate Similarity	NPD5110	Phase 2
0.7333	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4017	Approved
0.731	Intermediate Similarity	NPD3705	Approved
0.7299	Intermediate Similarity	NPD7309	Approved
0.7297	Intermediate Similarity	NPD7905	Discontinued
0.7296	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8095	Phase 1
0.7292	Intermediate Similarity	NPD2667	Approved
0.7292	Intermediate Similarity	NPD2668	Approved
0.729	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2922	Phase 1
0.7278	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6667	Approved
0.7278	Intermediate Similarity	NPD6666	Approved
0.7256	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6090	Discontinued
0.7239	Intermediate Similarity	NPD4773	Phase 2
0.7239	Intermediate Similarity	NPD4772	Phase 2
0.7226	Intermediate Similarity	NPD2161	Phase 2
0.7222	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2219	Phase 1
0.7215	Intermediate Similarity	NPD3692	Discontinued
0.7211	Intermediate Similarity	NPD1669	Approved
0.7203	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4908	Phase 1
0.72	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7298	Approved
0.7183	Intermediate Similarity	NPD2557	Approved
0.7182	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2556	Approved
0.7172	Intermediate Similarity	NPD2554	Approved
0.7171	Intermediate Similarity	NPD3532	Approved
0.7171	Intermediate Similarity	NPD3530	Approved
0.7171	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3531	Approved
0.7169	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2156	Approved
0.7161	Intermediate Similarity	NPD2154	Approved
0.7161	Intermediate Similarity	NPD2155	Approved
0.7158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7533	Approved
0.7153	Intermediate Similarity	NPD7534	Approved
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD2978	Approved
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD2977	Approved
0.7143	Intermediate Similarity	NPD1350	Approved
0.7143	Intermediate Similarity	NPD1351	Approved
0.7143	Intermediate Similarity	NPD1349	Approved
0.7143	Intermediate Similarity	NPD2971	Approved
0.7143	Intermediate Similarity	NPD2968	Approved
0.7134	Intermediate Similarity	NPD2170	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3596	Phase 2
0.7125	Intermediate Similarity	NPD1774	Approved
0.7124	Intermediate Similarity	NPD6225	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4476	Approved
0.7115	Intermediate Similarity	NPD3539	Phase 1
0.7115	Intermediate Similarity	NPD4477	Approved
0.7115	Intermediate Similarity	NPD6032	Approved
0.7105	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3049	Approved
0.7099	Intermediate Similarity	NPD3639	Approved
0.7099	Intermediate Similarity	NPD2122	Discontinued
0.7099	Intermediate Similarity	NPD3641	Approved
0.7099	Intermediate Similarity	NPD3640	Phase 3
0.7091	Intermediate Similarity	NPD5720	Discontinued
0.7088	Intermediate Similarity	NPD2974	Approved
0.7088	Intermediate Similarity	NPD2973	Approved
0.7088	Intermediate Similarity	NPD2975	Approved
0.7086	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5709	Phase 3
0.7081	Intermediate Similarity	NPD5006	Approved
0.7081	Intermediate Similarity	NPD5005	Approved
0.7079	Intermediate Similarity	NPD6841	Approved
0.7079	Intermediate Similarity	NPD6843	Phase 3
0.7079	Intermediate Similarity	NPD6842	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