NPASS Compound

Structure

NPC474200 OpenBabel07101719522D 28 31 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -4.3301 0.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 23 1 1 0 0 0 17 19 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 24 1 1 0 0 0 21 25 1 0 0 0 0 21 26 1 0 0 0 0 21 28 2 0 0 0 0 23 24 1 1 0 0 0 24 13 1 1 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	401.24
Volume:	425.975
LogP:	6.562
LogD:	4.741
LogS:	-6.951
# Rotatable Bonds:	3
TPSA:	21.7
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	4.634
Fsp3:	0.708
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:	-4.837
MDCK Permeability:	1.3919613593316171e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.18
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.367
Plasma Protein Binding (PPB):	95.94923400878906%
Volume Distribution (VD):	1.059
Pgp-substrate:	2.9138569831848145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.633
CYP2C19-inhibitor:	0.857
CYP2C19-substrate:	0.965
CYP2C9-inhibitor:	0.656
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.383
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.942
CYP3A4-substrate:	0.711

ADMET: Excretion

Clearance (CL):	10.472
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.634
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.761
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.797
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.479
Carcinogencity:	0.548
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC474200

Natural Product ID:	NPC474200
*Common Name:**	DRTPUUQCYHYPIT-FOEAQLGISA-N
IUPAC Name:	n.a.
Synonyms:	Aureol N,N-Dimethyl Thiocarbamate
Standard InCHIKey:	DRTPUUQCYHYPIT-FOEAQLGISA-N
Standard InCHI:	InChI=1S/C24H35NO2S/c1-16-8-11-20-22(2,3)12-7-13-24(20)23(16,4)15-17-14-18(9-10-19(17)27-24)26-21(28)25(5)6/h9-10,14,16,20H,7-8,11-13,15H2,1-6H3/t16-,20-,23+,24-/m0/s1
SMILES:	CC1CCC2C(CCCC23C1(CC4=C(O3)C=CC(=C4)OC(=S)N(C)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463442
PubChem CID:	5270653
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO20958	Smenospongia aurea	Species	Thorectidae	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	1
MIC	1
Others	3

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.087	ug.mL-1	PMID[552575]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	100.0	%	PMID[552575]
NPT2	Others	Unspecified		Selectivity Index	>	55.0	n.a.	PMID[552575]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	<	6.25	ug.mL-1	PMID[552575]

☑ 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 NPC474200 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	389
0.1-0.2	1827
0.2-0.3	4618
0.3-0.4	12184
0.4-0.5	7176
0.5-0.6	12820
0.6-0.7	3512
0.7-0.8	152
0.8-0.85	14
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.904	High Similarity	NPC475839
0.8692	High Similarity	NPC128321
0.8682	High Similarity	NPC248557
0.8561	High Similarity	NPC47288
0.837	Intermediate Similarity	NPC153019
0.8248	Intermediate Similarity	NPC211352
0.8175	Intermediate Similarity	NPC289624
0.8175	Intermediate Similarity	NPC27578
0.8148	Intermediate Similarity	NPC176590
0.8106	Intermediate Similarity	NPC473464
0.8106	Intermediate Similarity	NPC476332
0.8092	Intermediate Similarity	NPC212559
0.8077	Intermediate Similarity	NPC51341
0.8071	Intermediate Similarity	NPC474610
0.803	Intermediate Similarity	NPC168707
0.803	Intermediate Similarity	NPC48623
0.7985	Intermediate Similarity	NPC61685
0.7958	Intermediate Similarity	NPC265335
0.7955	Intermediate Similarity	NPC45663
0.7939	Intermediate Similarity	NPC471449
0.7923	Intermediate Similarity	NPC238176
0.7923	Intermediate Similarity	NPC187993
0.7902	Intermediate Similarity	NPC473049
0.7902	Intermediate Similarity	NPC472794
0.7902	Intermediate Similarity	NPC76312
0.7902	Intermediate Similarity	NPC79372
0.7899	Intermediate Similarity	NPC473048
0.7847	Intermediate Similarity	NPC472792
0.7847	Intermediate Similarity	NPC472791
0.7846	Intermediate Similarity	NPC69539
0.781	Intermediate Similarity	NPC156298
0.7769	Intermediate Similarity	NPC283169
0.7744	Intermediate Similarity	NPC474131
0.7727	Intermediate Similarity	NPC139047
0.771	Intermediate Similarity	NPC312105
0.7698	Intermediate Similarity	NPC96719
0.7698	Intermediate Similarity	NPC222108
0.7687	Intermediate Similarity	NPC474599
0.7671	Intermediate Similarity	NPC323126
0.7669	Intermediate Similarity	NPC32152
0.766	Intermediate Similarity	NPC325568
0.7655	Intermediate Similarity	NPC252901
0.7634	Intermediate Similarity	NPC473718
0.7619	Intermediate Similarity	NPC30416
0.7612	Intermediate Similarity	NPC232295
0.7597	Intermediate Similarity	NPC77772
0.7576	Intermediate Similarity	NPC236070
0.7576	Intermediate Similarity	NPC126759
0.7576	Intermediate Similarity	NPC141001
0.7576	Intermediate Similarity	NPC33900
0.7576	Intermediate Similarity	NPC242580
0.7574	Intermediate Similarity	NPC188997
0.7554	Intermediate Similarity	NPC186889
0.754	Intermediate Similarity	NPC475269
0.7538	Intermediate Similarity	NPC177962
0.7538	Intermediate Similarity	NPC62867
0.7538	Intermediate Similarity	NPC474920
0.7536	Intermediate Similarity	NPC133407
0.7536	Intermediate Similarity	NPC28476
0.7535	Intermediate Similarity	NPC85595
0.7534	Intermediate Similarity	NPC476191
0.7519	Intermediate Similarity	NPC238075
0.7519	Intermediate Similarity	NPC25648
0.7518	Intermediate Similarity	NPC261992
0.7518	Intermediate Similarity	NPC249425
0.7518	Intermediate Similarity	NPC196193
0.7517	Intermediate Similarity	NPC90645
0.748	Intermediate Similarity	NPC326801
0.7467	Intermediate Similarity	NPC475872
0.7465	Intermediate Similarity	NPC258073
0.7464	Intermediate Similarity	NPC474237
0.7463	Intermediate Similarity	NPC283616
0.7462	Intermediate Similarity	NPC266937
0.7462	Intermediate Similarity	NPC275627
0.7462	Intermediate Similarity	NPC470770
0.7447	Intermediate Similarity	NPC206028
0.7445	Intermediate Similarity	NPC152946
0.7445	Intermediate Similarity	NPC204535
0.7445	Intermediate Similarity	NPC46586
0.7431	Intermediate Similarity	NPC71372
0.7426	Intermediate Similarity	NPC129176
0.7424	Intermediate Similarity	NPC471534
0.7405	Intermediate Similarity	NPC280760
0.7405	Intermediate Similarity	NPC98372
0.74	Intermediate Similarity	NPC472457
0.7391	Intermediate Similarity	NPC474130
0.7381	Intermediate Similarity	NPC24327
0.7381	Intermediate Similarity	NPC12870
0.7379	Intermediate Similarity	NPC327382
0.7376	Intermediate Similarity	NPC223912
0.7368	Intermediate Similarity	NPC212142
0.7353	Intermediate Similarity	NPC135467
0.7353	Intermediate Similarity	NPC260832
0.7343	Intermediate Similarity	NPC472590
0.7338	Intermediate Similarity	NPC276962
0.7338	Intermediate Similarity	NPC75432
0.7338	Intermediate Similarity	NPC190086
0.7329	Intermediate Similarity	NPC21797
0.7329	Intermediate Similarity	NPC265515
0.7329	Intermediate Similarity	NPC194847
0.7328	Intermediate Similarity	NPC470723
0.7324	Intermediate Similarity	NPC472797
0.7324	Intermediate Similarity	NPC16577
0.7315	Intermediate Similarity	NPC186033
0.7305	Intermediate Similarity	NPC473134
0.7292	Intermediate Similarity	NPC469611
0.7292	Intermediate Similarity	NPC472798
0.7287	Intermediate Similarity	NPC320439
0.7286	Intermediate Similarity	NPC76119
0.7286	Intermediate Similarity	NPC252962
0.7286	Intermediate Similarity	NPC4286
0.7279	Intermediate Similarity	NPC474530
0.7279	Intermediate Similarity	NPC474521
0.7279	Intermediate Similarity	NPC323074
0.7279	Intermediate Similarity	NPC474540
0.7273	Intermediate Similarity	NPC158784
0.7273	Intermediate Similarity	NPC475102
0.7273	Intermediate Similarity	NPC195561
0.7273	Intermediate Similarity	NPC196621
0.7273	Intermediate Similarity	NPC475880
0.7273	Intermediate Similarity	NPC472793
0.7266	Intermediate Similarity	NPC96940
0.7248	Intermediate Similarity	NPC474851
0.7248	Intermediate Similarity	NPC474850
0.7241	Intermediate Similarity	NPC469610
0.7237	Intermediate Similarity	NPC471608
0.723	Intermediate Similarity	NPC19869
0.7226	Intermediate Similarity	NPC325544
0.7226	Intermediate Similarity	NPC477037
0.7226	Intermediate Similarity	NPC321133
0.7226	Intermediate Similarity	NPC318581
0.7226	Intermediate Similarity	NPC2745
0.7226	Intermediate Similarity	NPC302915
0.7222	Intermediate Similarity	NPC8899
0.7222	Intermediate Similarity	NPC160623
0.7222	Intermediate Similarity	NPC473047
0.7219	Intermediate Similarity	NPC316691
0.7214	Intermediate Similarity	NPC147896
0.7211	Intermediate Similarity	NPC472800
0.7203	Intermediate Similarity	NPC266868
0.7203	Intermediate Similarity	NPC472796
0.7203	Intermediate Similarity	NPC472795
0.72	Intermediate Similarity	NPC470161
0.7194	Intermediate Similarity	NPC302211
0.7185	Intermediate Similarity	NPC471668
0.7181	Intermediate Similarity	NPC221134
0.7179	Intermediate Similarity	NPC157783
0.7179	Intermediate Similarity	NPC325860
0.7174	Intermediate Similarity	NPC277798
0.7174	Intermediate Similarity	NPC473875
0.7174	Intermediate Similarity	NPC100108
0.7174	Intermediate Similarity	NPC322569
0.7171	Intermediate Similarity	NPC292256
0.7171	Intermediate Similarity	NPC471600
0.7162	Intermediate Similarity	NPC306365
0.7162	Intermediate Similarity	NPC471542
0.7154	Intermediate Similarity	NPC233320
0.7153	Intermediate Similarity	NPC11089
0.7153	Intermediate Similarity	NPC234956
0.7133	Intermediate Similarity	NPC38604
0.7133	Intermediate Similarity	NPC211179
0.7133	Intermediate Similarity	NPC81261
0.7133	Intermediate Similarity	NPC201069
0.7133	Intermediate Similarity	NPC283079
0.7124	Intermediate Similarity	NPC475896
0.7103	Intermediate Similarity	NPC211413
0.7103	Intermediate Similarity	NPC118683
0.7103	Intermediate Similarity	NPC474246
0.7103	Intermediate Similarity	NPC474143
0.7103	Intermediate Similarity	NPC293203
0.7103	Intermediate Similarity	NPC68205
0.7103	Intermediate Similarity	NPC244888
0.7103	Intermediate Similarity	NPC164804
0.7101	Intermediate Similarity	NPC103916
0.7092	Intermediate Similarity	NPC294156
0.7092	Intermediate Similarity	NPC256015
0.7083	Intermediate Similarity	NPC210655
0.7083	Intermediate Similarity	NPC93962
0.7083	Intermediate Similarity	NPC59654
0.7083	Intermediate Similarity	NPC271832
0.7077	Intermediate Similarity	NPC155072
0.7077	Intermediate Similarity	NPC53740
0.7075	Intermediate Similarity	NPC474478
0.7075	Intermediate Similarity	NPC27394
0.7075	Intermediate Similarity	NPC473107
0.7071	Intermediate Similarity	NPC478058
0.7067	Intermediate Similarity	NPC198038
0.7063	Intermediate Similarity	NPC95034
0.7063	Intermediate Similarity	NPC142087
0.7063	Intermediate Similarity	NPC98745
0.7063	Intermediate Similarity	NPC46978
0.7059	Intermediate Similarity	NPC9341
0.7059	Intermediate Similarity	NPC290470
0.7059	Intermediate Similarity	NPC81067
0.7059	Intermediate Similarity	NPC154256
0.7055	Intermediate Similarity	NPC189482
0.705	Intermediate Similarity	NPC96423
0.705	Intermediate Similarity	NPC218753
0.7047	Intermediate Similarity	NPC98804
0.7042	Intermediate Similarity	NPC279118

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 NPC474200 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	1030
0.2-0.3	1008
0.3-0.4	2852
0.4-0.5	2230
0.5-0.6	1266
0.6-0.7	480
0.7-0.8	45
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7907	Intermediate Similarity	NPD6671	Approved
0.7778	Intermediate Similarity	NPD5327	Phase 3
0.777	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7294	Phase 1
0.7704	Intermediate Similarity	NPD2232	Approved
0.7704	Intermediate Similarity	NPD2233	Approved
0.7704	Intermediate Similarity	NPD2230	Approved
0.7681	Intermediate Similarity	NPD2237	Approved
0.7669	Intermediate Similarity	NPD3443	Approved
0.7669	Intermediate Similarity	NPD3445	Approved
0.7669	Intermediate Similarity	NPD3444	Approved
0.7664	Intermediate Similarity	NPD4098	Discontinued
0.766	Intermediate Similarity	NPD3110	Approved
0.766	Intermediate Similarity	NPD3109	Approved
0.7591	Intermediate Similarity	NPD6696	Suspended
0.7576	Intermediate Similarity	NPD7340	Approved
0.7537	Intermediate Similarity	NPD6382	Discontinued
0.7519	Intermediate Similarity	NPD7644	Approved
0.75	Intermediate Similarity	NPD2557	Approved
0.75	Intermediate Similarity	NPD1611	Approved
0.7448	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7119	Phase 2
0.7357	Intermediate Similarity	NPD6584	Phase 3
0.7348	Intermediate Similarity	NPD1398	Phase 1
0.7343	Intermediate Similarity	NPD4475	Approved
0.7343	Intermediate Similarity	NPD4474	Approved
0.7343	Intermediate Similarity	NPD8032	Phase 2
0.7338	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6580	Approved
0.7333	Intermediate Similarity	NPD6581	Approved
0.7324	Intermediate Similarity	NPD4625	Phase 3
0.7315	Intermediate Similarity	NPD7466	Approved
0.731	Intermediate Similarity	NPD6353	Approved
0.7305	Intermediate Similarity	NPD2861	Phase 2
0.7303	Intermediate Similarity	NPD6090	Discontinued
0.7297	Intermediate Similarity	NPD7037	Approved
0.7266	Intermediate Similarity	NPD4749	Approved
0.7241	Intermediate Similarity	NPD4618	Approved
0.7241	Intermediate Similarity	NPD5735	Approved
0.7241	Intermediate Similarity	NPD4622	Approved
0.7239	Intermediate Similarity	NPD709	Approved
0.7239	Intermediate Similarity	NPD6387	Discontinued
0.7234	Intermediate Similarity	NPD4624	Approved
0.7234	Intermediate Similarity	NPD7905	Discontinued
0.723	Intermediate Similarity	NPD7030	Discontinued
0.7226	Intermediate Similarity	NPD2668	Approved
0.7226	Intermediate Similarity	NPD2667	Approved
0.7222	Intermediate Similarity	NPD7265	Discontinued
0.7206	Intermediate Similarity	NPD2486	Discontinued
0.72	Intermediate Similarity	NPD5754	Discontinued
0.7192	Intermediate Similarity	NPD4097	Suspended
0.7192	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3596	Phase 2
0.7172	Intermediate Similarity	NPD2238	Phase 2
0.7172	Intermediate Similarity	NPD4140	Approved
0.7162	Intermediate Similarity	NPD6100	Approved
0.7162	Intermediate Similarity	NPD6099	Approved
0.7153	Intermediate Similarity	NPD5585	Approved
0.7153	Intermediate Similarity	NPD3049	Approved
0.7143	Intermediate Similarity	NPD5689	Approved
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7143	Intermediate Similarity	NPD5688	Approved
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7089	Intermediate Similarity	NPD5929	Approved
0.7083	Intermediate Similarity	NPD7095	Approved
0.7063	Intermediate Similarity	NPD1712	Approved
0.705	Intermediate Similarity	NPD3496	Discontinued
0.705	Intermediate Similarity	NPD3447	Discontinued
0.705	Intermediate Similarity	NPD3294	Phase 2
0.7034	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5691	Approved
0.7025	Intermediate Similarity	NPD5722	Discontinued
0.7021	Intermediate Similarity	NPD6539	Approved
0.7021	Intermediate Similarity	NPD6540	Phase 3
0.7021	Intermediate Similarity	NPD6543	Approved
0.7021	Intermediate Similarity	NPD6542	Approved
0.702	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5535	Approved
0.7015	Intermediate Similarity	NPD7635	Approved
0.7014	Intermediate Similarity	NPD4908	Phase 1
0.7014	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5085	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3051	Approved
0.6993	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7477	Discontinued
0.6985	Remote Similarity	NPD7157	Approved
0.6978	Remote Similarity	NPD2554	Approved
0.6978	Remote Similarity	NPD2556	Approved
0.6978	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6538	Approved
0.6972	Remote Similarity	NPD6541	Approved
0.6968	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5283	Phase 1
0.6959	Remote Similarity	NPD2157	Approved
0.6957	Remote Similarity	NPD7831	Phase 2
0.6957	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7833	Phase 2
0.6954	Remote Similarity	NPD2897	Discontinued
0.695	Remote Similarity	NPD2231	Phase 2
0.695	Remote Similarity	NPD2235	Phase 2
0.6948	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4477	Approved
0.6933	Remote Similarity	NPD6032	Approved
0.6933	Remote Similarity	NPD4476	Approved
0.6923	Remote Similarity	NPD7427	Discontinued
0.6923	Remote Similarity	NPD4727	Phase 1
0.6923	Remote Similarity	NPD5699	Approved
0.6918	Remote Similarity	NPD1336	Approved
0.6913	Remote Similarity	NPD6896	Approved
0.6913	Remote Similarity	NPD6895	Approved
0.6913	Remote Similarity	NPD2200	Suspended
0.6903	Remote Similarity	NPD7019	Approved
0.6903	Remote Similarity	NPD7020	Approved
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4359	Approved
0.6901	Remote Similarity	NPD1669	Approved
0.6897	Remote Similarity	NPD2606	Approved
0.6897	Remote Similarity	NPD2605	Approved
0.6892	Remote Similarity	NPD3657	Discovery
0.6879	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7018	Phase 2
0.6871	Remote Similarity	NPD4870	Approved
0.6867	Remote Similarity	NPD2154	Approved
0.6867	Remote Similarity	NPD4108	Discontinued
0.6867	Remote Similarity	NPD2156	Approved
0.6867	Remote Similarity	NPD2155	Approved
0.6863	Remote Similarity	NPD6748	Discontinued
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4626	Approved
0.6853	Remote Similarity	NPD8651	Approved
0.6849	Remote Similarity	NPD5155	Approved
0.6849	Remote Similarity	NPD5156	Approved
0.6848	Remote Similarity	NPD2970	Approved
0.6848	Remote Similarity	NPD2969	Approved
0.6832	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4060	Phase 1
0.6822	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3301	Approved
0.6818	Remote Similarity	NPD968	Approved
0.6818	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3692	Discontinued
0.6813	Remote Similarity	NPD5714	Approved
0.6813	Remote Similarity	NPD6844	Discontinued
0.6807	Remote Similarity	NPD2489	Approved
0.6807	Remote Similarity	NPD4481	Phase 3
0.6807	Remote Similarity	NPD27	Approved
0.6803	Remote Similarity	NPD7985	Registered
0.6803	Remote Similarity	NPD5718	Phase 2
0.68	Remote Similarity	NPD7097	Phase 1
0.6797	Remote Similarity	NPD5177	Phase 3
0.6797	Remote Similarity	NPD6674	Discontinued
0.6795	Remote Similarity	NPD7447	Phase 1
0.6792	Remote Similarity	NPD5713	Approved
0.6791	Remote Similarity	NPD1792	Phase 2
0.6791	Remote Similarity	NPD5451	Approved
0.6786	Remote Similarity	NPD1651	Approved
0.6786	Remote Similarity	NPD4093	Discontinued
0.6781	Remote Similarity	NPD3595	Approved
0.6781	Remote Similarity	NPD3594	Approved
0.6776	Remote Similarity	NPD5763	Approved
0.6776	Remote Similarity	NPD5762	Approved
0.6774	Remote Similarity	NPD6815	Approved
0.6774	Remote Similarity	NPD6666	Approved
0.6774	Remote Similarity	NPD6667	Approved
0.6761	Remote Similarity	NPD1610	Phase 2
0.6753	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2675	Approved
0.6752	Remote Similarity	NPD2676	Approved
0.6741	Remote Similarity	NPD2673	Approved
0.6741	Remote Similarity	NPD2671	Approved
0.6738	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1751	Approved
0.6738	Remote Similarity	NPD17	Approved
0.6738	Remote Similarity	NPD1778	Approved
0.6732	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3124	Discontinued
0.6731	Remote Similarity	NPD7598	Phase 2
0.6731	Remote Similarity	NPD6087	Phase 1
0.6724	Remote Similarity	NPD7906	Approved
0.6716	Remote Similarity	NPD2684	Approved
0.6715	Remote Similarity	NPD594	Approved
0.6715	Remote Similarity	NPD592	Approved
0.6713	Remote Similarity	NPD1840	Phase 2
0.6713	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3635	Approved
0.6712	Remote Similarity	NPD3637	Approved
0.6712	Remote Similarity	NPD3636	Approved
0.6711	Remote Similarity	NPD6225	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3620	Phase 2
0.6711	Remote Similarity	NPD2979	Phase 3
0.671	Remote Similarity	NPD2677	Approved
0.6709	Remote Similarity	NPD1914	Approved
0.6708	Remote Similarity	NPD7248	Discontinued

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