NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	435.13
Volume:	427.042
LogP:	3.499
LogD:	2.559
LogS:	-6.209
# Rotatable Bonds:	2
TPSA:	126.18
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	4.086
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.019
MDCK Permeability:	1.2415223864081781e-05
Pgp-inhibitor:	0.694
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.155
Plasma Protein Binding (PPB):	96.04236602783203%
Volume Distribution (VD):	0.771
Pgp-substrate:	1.605657696723938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.763
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.58
CYP2C9-substrate:	0.506
CYP2D6-inhibitor:	0.209
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.297
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	10.302
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.461
Human Hepatotoxicity (H-HT):	0.302
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.919
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.263
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.368
Respiratory Toxicity:	0.375

Download Data

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

Natural Product: NPC478045

Natural Product ID:	NPC478045
*Common Name:**	L-digitoxosyl-phenanthroviridin
IUPAC Name:	8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-3-methylbenzo[b]phenanthridine-7,12-dione
Synonyms:
Standard InCHIKey:	RHJZSFGUTPCBSW-GAUMXTCASA-N
Standard InCHI:	InChI=1S/C24H21NO7/c1-10-6-12-9-25-21-20(18(12)14(26)7-10)23(29)13-4-3-5-16(19(13)24(21)30)32-17-8-15(27)22(28)11(2)31-17/h3-7,9,11,15,17,22,26-28H,8H2,1-2H3/t11-,15+,17-,22-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@@H](C[C@@H](O1)OC2=CC=CC3=C2C(=O)C4=NC=C5C=C(C=C(C5=C4C3=O)O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122182600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

*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
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11720530]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724858]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[21774474]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22050382]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[23164710]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26203536]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	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
GI50	1
Others	2

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	GI50	=	2140	nM	PMID[26203536]
NPT2	Others	Unspecified	TGI	=	5750	nM	PMID[26203536]
NPT2	Others	Unspecified	LC50	=	18200	nM	PMID[26203536]

☑ 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 NPC478045 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	456
0.1-0.2	2104
0.2-0.3	7125
0.3-0.4	10148
0.4-0.5	8177
0.5-0.6	11910
0.6-0.7	2504
0.7-0.8	260
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8382	Intermediate Similarity	NPC183537
0.8354	Intermediate Similarity	NPC210296
0.8306	Intermediate Similarity	NPC77878
0.827	Intermediate Similarity	NPC166722
0.8228	Intermediate Similarity	NPC189903
0.8228	Intermediate Similarity	NPC182907
0.8208	Intermediate Similarity	NPC15406
0.8186	Intermediate Similarity	NPC108342
0.8174	Intermediate Similarity	NPC124313
0.8128	Intermediate Similarity	NPC24019
0.8101	Intermediate Similarity	NPC22481
0.8091	Intermediate Similarity	NPC207283
0.8091	Intermediate Similarity	NPC84164
0.7992	Intermediate Similarity	NPC90875
0.7975	Intermediate Similarity	NPC278525
0.7918	Intermediate Similarity	NPC107123
0.7908	Intermediate Similarity	NPC233334
0.7872	Intermediate Similarity	NPC210434
0.7839	Intermediate Similarity	NPC94842
0.7826	Intermediate Similarity	NPC220337
0.7755	Intermediate Similarity	NPC119134
0.7588	Intermediate Similarity	NPC471978
0.7578	Intermediate Similarity	NPC473833
0.7574	Intermediate Similarity	NPC146976
0.7532	Intermediate Similarity	NPC236668
0.7532	Intermediate Similarity	NPC232225
0.7531	Intermediate Similarity	NPC253314
0.75	Intermediate Similarity	NPC471979
0.749	Intermediate Similarity	NPC170101
0.749	Intermediate Similarity	NPC132385
0.748	Intermediate Similarity	NPC475648
0.7479	Intermediate Similarity	NPC470020
0.747	Intermediate Similarity	NPC134637
0.7469	Intermediate Similarity	NPC322482
0.7468	Intermediate Similarity	NPC478048
0.7461	Intermediate Similarity	NPC13603
0.7452	Intermediate Similarity	NPC328928
0.7451	Intermediate Similarity	NPC471015
0.745	Intermediate Similarity	NPC208522
0.7449	Intermediate Similarity	NPC211920
0.7441	Intermediate Similarity	NPC137353
0.7437	Intermediate Similarity	NPC321226
0.7437	Intermediate Similarity	NPC478046
0.7437	Intermediate Similarity	NPC478047
0.7437	Intermediate Similarity	NPC180210
0.7437	Intermediate Similarity	NPC314914
0.7437	Intermediate Similarity	NPC328856
0.7431	Intermediate Similarity	NPC270515
0.743	Intermediate Similarity	NPC253482
0.7422	Intermediate Similarity	NPC85879
0.7422	Intermediate Similarity	NPC475301
0.7422	Intermediate Similarity	NPC326930
0.7422	Intermediate Similarity	NPC53255
0.7418	Intermediate Similarity	NPC246381
0.7406	Intermediate Similarity	NPC284236
0.7406	Intermediate Similarity	NPC316368
0.7403	Intermediate Similarity	NPC129897
0.7381	Intermediate Similarity	NPC148896
0.7381	Intermediate Similarity	NPC180668
0.7381	Intermediate Similarity	NPC471013
0.7377	Intermediate Similarity	NPC124029
0.7355	Intermediate Similarity	NPC216612
0.7355	Intermediate Similarity	NPC122463
0.7355	Intermediate Similarity	NPC118121
0.735	Intermediate Similarity	NPC193238
0.7344	Intermediate Similarity	NPC469439
0.7342	Intermediate Similarity	NPC111732
0.7336	Intermediate Similarity	NPC473506
0.7333	Intermediate Similarity	NPC204446
0.7333	Intermediate Similarity	NPC10904
0.7328	Intermediate Similarity	NPC30456
0.7306	Intermediate Similarity	NPC74575
0.7302	Intermediate Similarity	NPC72905
0.7295	Intermediate Similarity	NPC477902
0.7287	Intermediate Similarity	NPC475303
0.7287	Intermediate Similarity	NPC150698
0.7287	Intermediate Similarity	NPC316841
0.7287	Intermediate Similarity	NPC96801
0.7287	Intermediate Similarity	NPC475596
0.7276	Intermediate Similarity	NPC475644
0.7276	Intermediate Similarity	NPC471190
0.7276	Intermediate Similarity	NPC471977
0.7276	Intermediate Similarity	NPC470486
0.7273	Intermediate Similarity	NPC142385
0.7269	Intermediate Similarity	NPC253675
0.7269	Intermediate Similarity	NPC35208
0.7269	Intermediate Similarity	NPC475406
0.7269	Intermediate Similarity	NPC475426
0.7269	Intermediate Similarity	NPC327769
0.7265	Intermediate Similarity	NPC470018
0.7259	Intermediate Similarity	NPC472589
0.7258	Intermediate Similarity	NPC49547
0.7255	Intermediate Similarity	NPC475315
0.7255	Intermediate Similarity	NPC324619
0.724	Intermediate Similarity	NPC38959
0.724	Intermediate Similarity	NPC327904
0.7237	Intermediate Similarity	NPC302807
0.7236	Intermediate Similarity	NPC87152
0.7236	Intermediate Similarity	NPC475631
0.7236	Intermediate Similarity	NPC228377
0.7236	Intermediate Similarity	NPC328186
0.7236	Intermediate Similarity	NPC122968
0.7236	Intermediate Similarity	NPC475600
0.7236	Intermediate Similarity	NPC477787
0.7236	Intermediate Similarity	NPC476110
0.7229	Intermediate Similarity	NPC237702
0.7229	Intermediate Similarity	NPC96584
0.7229	Intermediate Similarity	NPC255800
0.722	Intermediate Similarity	NPC472435
0.7218	Intermediate Similarity	NPC292416
0.7218	Intermediate Similarity	NPC473689
0.7218	Intermediate Similarity	NPC477906
0.7216	Intermediate Similarity	NPC475533
0.7197	Intermediate Similarity	NPC251160
0.7189	Intermediate Similarity	NPC471004
0.7189	Intermediate Similarity	NPC320324
0.7189	Intermediate Similarity	NPC319880
0.7189	Intermediate Similarity	NPC244839
0.7184	Intermediate Similarity	NPC471980
0.7181	Intermediate Similarity	NPC472588
0.7178	Intermediate Similarity	NPC30570
0.7176	Intermediate Similarity	NPC476090
0.7172	Intermediate Similarity	NPC477903
0.7169	Intermediate Similarity	NPC314222
0.7169	Intermediate Similarity	NPC196449
0.7154	Intermediate Similarity	NPC475137
0.7154	Intermediate Similarity	NPC473850
0.7154	Intermediate Similarity	NPC475498
0.7149	Intermediate Similarity	NPC162812
0.7143	Intermediate Similarity	NPC470022
0.7143	Intermediate Similarity	NPC127720
0.7143	Intermediate Similarity	NPC127026
0.7137	Intermediate Similarity	NPC475362
0.7137	Intermediate Similarity	NPC472436
0.7137	Intermediate Similarity	NPC235076
0.7131	Intermediate Similarity	NPC156044
0.7126	Intermediate Similarity	NPC318068
0.7125	Intermediate Similarity	NPC292517
0.712	Intermediate Similarity	NPC469748
0.7119	Intermediate Similarity	NPC100079
0.7119	Intermediate Similarity	NPC23614
0.7114	Intermediate Similarity	NPC57797
0.7114	Intermediate Similarity	NPC250807
0.7114	Intermediate Similarity	NPC76565
0.7113	Intermediate Similarity	NPC188420
0.7104	Intermediate Similarity	NPC473800
0.7103	Intermediate Similarity	NPC470017
0.7097	Intermediate Similarity	NPC475601
0.7097	Intermediate Similarity	NPC146824
0.7095	Intermediate Similarity	NPC271215
0.7095	Intermediate Similarity	NPC149471
0.7092	Intermediate Similarity	NPC329631
0.709	Intermediate Similarity	NPC216428
0.709	Intermediate Similarity	NPC84815
0.709	Intermediate Similarity	NPC301368
0.7085	Intermediate Similarity	NPC328154
0.7082	Intermediate Similarity	NPC324245
0.7082	Intermediate Similarity	NPC320748
0.708	Intermediate Similarity	NPC201508
0.7073	Intermediate Similarity	NPC477788
0.707	Intermediate Similarity	NPC291609
0.7064	Intermediate Similarity	NPC328559
0.7064	Intermediate Similarity	NPC155792
0.7064	Intermediate Similarity	NPC32451
0.7059	Intermediate Similarity	NPC99891
0.7054	Intermediate Similarity	NPC161801
0.7049	Intermediate Similarity	NPC473822
0.7049	Intermediate Similarity	NPC62367
0.7049	Intermediate Similarity	NPC144779
0.7049	Intermediate Similarity	NPC294579
0.7046	Intermediate Similarity	NPC25442
0.7046	Intermediate Similarity	NPC12944
0.7045	Intermediate Similarity	NPC191489
0.7041	Intermediate Similarity	NPC227824
0.7039	Intermediate Similarity	NPC329024
0.7037	Intermediate Similarity	NPC42678
0.7037	Intermediate Similarity	NPC477907
0.7037	Intermediate Similarity	NPC477909
0.7033	Intermediate Similarity	NPC477912
0.7031	Intermediate Similarity	NPC44354
0.7031	Intermediate Similarity	NPC124300
0.7026	Intermediate Similarity	NPC101312
0.7021	Intermediate Similarity	NPC79223
0.702	Intermediate Similarity	NPC46451
0.7017	Intermediate Similarity	NPC309498
0.7016	Intermediate Similarity	NPC26881
0.7016	Intermediate Similarity	NPC310618
0.7016	Intermediate Similarity	NPC477900
0.7016	Intermediate Similarity	NPC477899
0.7009	Intermediate Similarity	NPC317672
0.7008	Intermediate Similarity	NPC6981
0.7004	Intermediate Similarity	NPC316224
0.6996	Remote Similarity	NPC264674
0.6996	Remote Similarity	NPC170751
0.6996	Remote Similarity	NPC473053
0.6992	Remote Similarity	NPC477901
0.6992	Remote Similarity	NPC148889
0.6991	Remote Similarity	NPC203751
0.6988	Remote Similarity	NPC148860
0.6987	Remote Similarity	NPC206186

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 NPC478045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	638
0.2-0.3	978
0.3-0.4	1945
0.4-0.5	2727
0.5-0.6	1967
0.6-0.7	583
0.7-0.8	31
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
0.7869	Intermediate Similarity	NPD1483	Discontinued
0.751	Intermediate Similarity	NPD3925	Approved
0.7489	Intermediate Similarity	NPD7069	Discontinued
0.747	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD5022	Discontinued
0.7333	Intermediate Similarity	NPD7395	Discontinued
0.7216	Intermediate Similarity	NPD5488	Discontinued
0.7195	Intermediate Similarity	NPD3263	Phase 3
0.7165	Intermediate Similarity	NPD8091	Phase 3
0.7149	Intermediate Similarity	NPD4989	Phase 2
0.7131	Intermediate Similarity	NPD8479	Phase 2
0.7126	Intermediate Similarity	NPD6790	Phase 1
0.7106	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4429	Discontinued
0.7045	Intermediate Similarity	NPD7708	Approved
0.704	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4373	Phase 2
0.702	Intermediate Similarity	NPD3763	Approved
0.7019	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD5482	Discontinued
0.6988	Remote Similarity	NPD7426	Phase 1
0.6987	Remote Similarity	NPD5429	Discontinued
0.6983	Remote Similarity	NPD5866	Approved
0.6953	Remote Similarity	NPD7885	Phase 2
0.6953	Remote Similarity	NPD7886	Phase 2
0.695	Remote Similarity	NPD8468	Phase 2
0.694	Remote Similarity	NPD7803	Approved
0.6926	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5640	Discontinued
0.692	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6530	Approved
0.6917	Remote Similarity	NPD6531	Approved
0.6911	Remote Similarity	NPD6568	Discontinued
0.6911	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7169	Suspended
0.6905	Remote Similarity	NPD4952	Phase 3
0.6902	Remote Similarity	NPD3006	Discontinued
0.6899	Remote Similarity	NPD6716	Phase 1
0.6895	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6494	Phase 2
0.6889	Remote Similarity	NPD7925	Phase 2
0.6889	Remote Similarity	NPD7924	Phase 2
0.6888	Remote Similarity	NPD7701	Phase 2
0.6885	Remote Similarity	NPD3794	Approved
0.6885	Remote Similarity	NPD3795	Approved
0.6872	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7654	Discontinued
0.686	Remote Similarity	NPD7417	Discontinued
0.6857	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3816	Phase 1
0.6844	Remote Similarity	NPD3815	Phase 1
0.6842	Remote Similarity	NPD1926	Approved
0.6838	Remote Similarity	NPD6361	Phase 2
0.6835	Remote Similarity	NPD6874	Approved
0.6833	Remote Similarity	NPD4122	Approved
0.6833	Remote Similarity	NPD4037	Approved
0.6833	Remote Similarity	NPD4034	Approved
0.6833	Remote Similarity	NPD4036	Approved
0.6833	Remote Similarity	NPD4039	Approved
0.6833	Remote Similarity	NPD4035	Approved
0.6833	Remote Similarity	NPD32	Approved
0.6833	Remote Similarity	NPD4038	Approved
0.6833	Remote Similarity	NPD4033	Approved
0.6833	Remote Similarity	NPD31	Approved
0.6825	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6974	Phase 3
0.6803	Remote Similarity	NPD5416	Discontinued
0.6802	Remote Similarity	NPD8325	Phase 3
0.6802	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8326	Phase 3
0.6797	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6825	Phase 1
0.6779	Remote Similarity	NPD8461	Discontinued
0.6777	Remote Similarity	NPD7584	Approved
0.6774	Remote Similarity	NPD6198	Phase 1
0.6758	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7955	Approved
0.6754	Remote Similarity	NPD7956	Approved
0.6753	Remote Similarity	NPD5450	Discontinued
0.675	Remote Similarity	NPD6823	Phase 2
0.6747	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6962	Phase 2
0.6737	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7801	Approved
0.6723	Remote Similarity	NPD6569	Phase 2
0.6723	Remote Similarity	NPD3924	Approved
0.6723	Remote Similarity	NPD3921	Approved
0.6723	Remote Similarity	NPD3922	Approved
0.6723	Remote Similarity	NPD3923	Approved
0.6722	Remote Similarity	NPD5513	Phase 2
0.6708	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3322	Phase 1
0.6705	Remote Similarity	NPD7853	Phase 2
0.6705	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6212	Phase 3
0.6695	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6213	Phase 3
0.6694	Remote Similarity	NPD7874	Approved
0.6694	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8059	Phase 3
0.6693	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4923	Phase 1
0.6681	Remote Similarity	NPD4889	Approved
0.6679	Remote Similarity	NPD6475	Phase 2
0.6678	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD7010	Phase 3
0.6667	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD5532	Phase 2
0.6667	Remote Similarity	NPD6778	Approved
0.6654	Remote Similarity	NPD6456	Discontinued
0.6653	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7922	Phase 1
0.6628	Remote Similarity	NPD7558	Phase 2
0.6627	Remote Similarity	NPD6298	Discontinued
0.6627	Remote Similarity	NPD7994	Phase 2
0.6626	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8367	Approved
0.6615	Remote Similarity	NPD5805	Approved
0.6615	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7467	Discontinued
0.6612	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD8370	Discontinued
0.6604	Remote Similarity	NPD6276	Discontinued
0.6601	Remote Similarity	NPD8356	Approved
0.6599	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4894	Discontinued
0.6588	Remote Similarity	NPD7674	Phase 3
0.6588	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7675	Phase 3
0.6587	Remote Similarity	NPD6242	Discontinued
0.6584	Remote Similarity	NPD7697	Approved
0.6584	Remote Similarity	NPD7698	Approved
0.6584	Remote Similarity	NPD7696	Phase 3
0.6581	Remote Similarity	NPD4375	Approved
0.658	Remote Similarity	NPD8492	Approved
0.6567	Remote Similarity	NPD8312	Approved
0.6567	Remote Similarity	NPD7859	Phase 2
0.6567	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD8313	Approved
0.6562	Remote Similarity	NPD4845	Discontinued
0.6562	Remote Similarity	NPD8430	Approved
0.6561	Remote Similarity	NPD5506	Approved
0.6561	Remote Similarity	NPD5507	Approved
0.6559	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5914	Approved
0.6557	Remote Similarity	NPD8319	Approved
0.6557	Remote Similarity	NPD8320	Phase 1
0.6557	Remote Similarity	NPD7870	Phase 2
0.6557	Remote Similarity	NPD7871	Phase 2
0.6554	Remote Similarity	NPD3809	Discontinued
0.6553	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8067	Phase 3
0.6549	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6376	Discontinued
0.6536	Remote Similarity	NPD3217	Phase 2
0.6534	Remote Similarity	NPD5459	Phase 2
0.653	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7031	Phase 1
0.6522	Remote Similarity	NPD7180	Phase 3
0.6522	Remote Similarity	NPD3280	Approved
0.652	Remote Similarity	NPD5293	Phase 2
0.6518	Remote Similarity	NPD4437	Phase 3
0.6517	Remote Similarity	NPD4369	Phase 2
0.6516	Remote Similarity	NPD7435	Discontinued
0.6513	Remote Similarity	NPD5891	Approved
0.6512	Remote Similarity	NPD7567	Approved
0.6511	Remote Similarity	NPD5922	Phase 3
0.6508	Remote Similarity	NPD3354	Phase 2
0.65	Remote Similarity	NPD5512	Phase 3
0.65	Remote Similarity	NPD3477	Phase 2
0.65	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5147	Discontinued
0.6496	Remote Similarity	NPD8366	Approved
0.6494	Remote Similarity	NPD3389	Approved
0.6494	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5612	Discontinued
0.6494	Remote Similarity	NPD3393	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