NPASS Compound

Structure

NPC5943 OpenBabel07101719252D 28 32 0 0 1 0 0 0 0 0999 V2000 -2.1704 -2.3932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8212 -4.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3944 -1.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1249 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0116 0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4922 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4416 0.1852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9222 0.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 2.4031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2219 -2.1916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8727 -3.8344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4416 1.7542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9222 -1.2693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 1.9394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5193 0.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5193 1.4545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8398 0.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2238 -4.5551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 2.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 1.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3944 0.8859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5730 -2.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 1 1 6 0 0 0 13 16 1 0 0 0 0 13 28 1 0 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 21 1 6 0 0 0 16 19 1 1 0 0 0 17 20 1 1 0 0 0 17 22 1 0 0 0 0 18 21 1 1 0 0 0 18 25 1 0 0 0 0 19 23 1 1 0 0 0 20 21 1 1 0 0 0 21 11 1 1 0 0 0 22 23 1 6 0 0 0 22 26 1 0 0 0 0 23 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.26
Volume:	404.897
LogP:	2.328
LogD:	2.097
LogS:	-3.721
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	5.51
Fsp3:	0.957
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.199
MDCK Permeability:	6.013536767568439e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	84.76529693603516%
Volume Distribution (VD):	0.737
Pgp-substrate:	8.740694999694824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.349
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	2.526
Half-life (T1/2):	0.521

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.882
Skin Sensitization:	0.868
Carcinogencity:	0.167
Eye Corrosion:	0.024
Eye Irritation:	0.135
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC5943

Natural Product ID:	NPC5943
*Common Name:**	Vladimuliecin B
IUPAC Name:	n.a.
Synonyms:	vladimuliecin B
Standard InCHIKey:	CZFZYEPCYFVTBZ-NWUCDKBLSA-N
Standard InCHI:	InChI=1S/C23H36O5/c1-13(28-14(2)24)16-6-10-23(27)19(16,3)9-7-17-20(4)8-5-15-11-21(15,20)18(25)12-22(17,23)26/h13,15-18,25-27H,5-12H2,1-4H3/t13-,15-,16-,17-,18-,19-,20-,21+,22+,23-/m1/s1
SMILES:	CC(=O)O[C@@H]([C@H]1CC[C@]2([C@]1(C)CC[C@H]1[C@@]2(O)C[C@H]([C@]23[C@]1(C)CC[C@@H]3C2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL565175
PubChem CID:	44179108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	88000.0	nM	PMID[515254]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	104300.0	nM	PMID[515254]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	120900.0	nM	PMID[515254]

☑ 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 NPC5943 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	413
0.1-0.2	3741
0.2-0.3	11684
0.3-0.4	12123
0.4-0.5	5796
0.5-0.6	5524
0.6-0.7	2772
0.7-0.8	557
0.8-0.85	65
0.85-0.9	18
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC131365
0.9277	High Similarity	NPC266651
0.9036	High Similarity	NPC69953
0.9012	High Similarity	NPC269333
0.8916	High Similarity	NPC154043
0.8916	High Similarity	NPC60018
0.8916	High Similarity	NPC202688
0.8902	High Similarity	NPC474714
0.8864	High Similarity	NPC473066
0.881	High Similarity	NPC2572
0.881	High Similarity	NPC29342
0.8721	High Similarity	NPC215968
0.8721	High Similarity	NPC155531
0.8556	High Similarity	NPC122083
0.8556	High Similarity	NPC256104
0.8556	High Similarity	NPC182740
0.8556	High Similarity	NPC211845
0.8554	High Similarity	NPC476176
0.8519	High Similarity	NPC186851
0.8506	High Similarity	NPC64862
0.8506	High Similarity	NPC477283
0.8478	Intermediate Similarity	NPC156377
0.8471	Intermediate Similarity	NPC477446
0.8471	Intermediate Similarity	NPC470155
0.8471	Intermediate Similarity	NPC475388
0.8471	Intermediate Similarity	NPC477447
0.8452	Intermediate Similarity	NPC472943
0.8452	Intermediate Similarity	NPC472951
0.8434	Intermediate Similarity	NPC471045
0.8372	Intermediate Similarity	NPC477285
0.8372	Intermediate Similarity	NPC111582
0.8353	Intermediate Similarity	NPC470154
0.8353	Intermediate Similarity	NPC470156
0.8333	Intermediate Similarity	NPC287452
0.8313	Intermediate Similarity	NPC105208
0.8313	Intermediate Similarity	NPC302578
0.8313	Intermediate Similarity	NPC192046
0.8313	Intermediate Similarity	NPC128951
0.8313	Intermediate Similarity	NPC477227
0.828	Intermediate Similarity	NPC116683
0.8256	Intermediate Similarity	NPC477286
0.8256	Intermediate Similarity	NPC286719
0.8242	Intermediate Similarity	NPC219516
0.8235	Intermediate Similarity	NPC117137
0.8235	Intermediate Similarity	NPC16449
0.8235	Intermediate Similarity	NPC66766
0.8214	Intermediate Similarity	NPC147993
0.8214	Intermediate Similarity	NPC67657
0.8214	Intermediate Similarity	NPC18857
0.8211	Intermediate Similarity	NPC470030
0.8202	Intermediate Similarity	NPC45833
0.8202	Intermediate Similarity	NPC472396
0.8202	Intermediate Similarity	NPC62202
0.8202	Intermediate Similarity	NPC110365
0.8202	Intermediate Similarity	NPC213658
0.8193	Intermediate Similarity	NPC163597
0.8171	Intermediate Similarity	NPC472944
0.8171	Intermediate Similarity	NPC475458
0.8171	Intermediate Similarity	NPC472945
0.814	Intermediate Similarity	NPC73515
0.814	Intermediate Similarity	NPC190940
0.8125	Intermediate Similarity	NPC476512
0.8125	Intermediate Similarity	NPC108227
0.8125	Intermediate Similarity	NPC472081
0.8118	Intermediate Similarity	NPC81074
0.8118	Intermediate Similarity	NPC477282
0.8111	Intermediate Similarity	NPC128475
0.8095	Intermediate Similarity	NPC185915
0.8095	Intermediate Similarity	NPC476233
0.8095	Intermediate Similarity	NPC171658
0.8072	Intermediate Similarity	NPC196136
0.8072	Intermediate Similarity	NPC317242
0.8072	Intermediate Similarity	NPC243027
0.8072	Intermediate Similarity	NPC158208
0.8068	Intermediate Similarity	NPC18953
0.8068	Intermediate Similarity	NPC474156
0.8068	Intermediate Similarity	NPC320824
0.8065	Intermediate Similarity	NPC151214
0.8065	Intermediate Similarity	NPC191915
0.8065	Intermediate Similarity	NPC470424
0.8046	Intermediate Similarity	NPC477284
0.8041	Intermediate Similarity	NPC310138
0.8041	Intermediate Similarity	NPC134967
0.8041	Intermediate Similarity	NPC114700
0.8041	Intermediate Similarity	NPC470029
0.8022	Intermediate Similarity	NPC228059
0.8	Intermediate Similarity	NPC161928
0.8	Intermediate Similarity	NPC471769
0.8	Intermediate Similarity	NPC210658
0.7979	Intermediate Similarity	NPC21897
0.7978	Intermediate Similarity	NPC273290
0.7978	Intermediate Similarity	NPC232044
0.7959	Intermediate Similarity	NPC97260
0.7959	Intermediate Similarity	NPC476837
0.7959	Intermediate Similarity	NPC139181
0.7957	Intermediate Similarity	NPC475307
0.7952	Intermediate Similarity	NPC304499
0.7952	Intermediate Similarity	NPC10476
0.7952	Intermediate Similarity	NPC228994
0.7952	Intermediate Similarity	NPC192501
0.7938	Intermediate Similarity	NPC475574
0.7938	Intermediate Similarity	NPC476838
0.7938	Intermediate Similarity	NPC476839
0.7935	Intermediate Similarity	NPC10274
0.7935	Intermediate Similarity	NPC77756
0.7917	Intermediate Similarity	NPC292775
0.7912	Intermediate Similarity	NPC470872
0.7912	Intermediate Similarity	NPC56777
0.7912	Intermediate Similarity	NPC201607
0.7912	Intermediate Similarity	NPC476379
0.7912	Intermediate Similarity	NPC476435
0.7907	Intermediate Similarity	NPC477287
0.7907	Intermediate Similarity	NPC220379
0.7895	Intermediate Similarity	NPC296936
0.7895	Intermediate Similarity	NPC292718
0.7895	Intermediate Similarity	NPC306797
0.7895	Intermediate Similarity	NPC111834
0.7895	Intermediate Similarity	NPC169270
0.7895	Intermediate Similarity	NPC252056
0.7889	Intermediate Similarity	NPC114378
0.7889	Intermediate Similarity	NPC472272
0.7889	Intermediate Similarity	NPC471240
0.7889	Intermediate Similarity	NPC103782
0.7882	Intermediate Similarity	NPC11907
0.7882	Intermediate Similarity	NPC133596
0.7882	Intermediate Similarity	NPC64081
0.7882	Intermediate Similarity	NPC474574
0.7882	Intermediate Similarity	NPC212453
0.7872	Intermediate Similarity	NPC113500
0.7872	Intermediate Similarity	NPC3538
0.7872	Intermediate Similarity	NPC39453
0.7872	Intermediate Similarity	NPC30687
0.7872	Intermediate Similarity	NPC477224
0.7872	Intermediate Similarity	NPC175
0.7865	Intermediate Similarity	NPC227260
0.7857	Intermediate Similarity	NPC139765
0.7857	Intermediate Similarity	NPC131584
0.7857	Intermediate Similarity	NPC472950
0.7857	Intermediate Similarity	NPC472952
0.7849	Intermediate Similarity	NPC293609
0.7849	Intermediate Similarity	NPC52756
0.7841	Intermediate Similarity	NPC470611
0.7841	Intermediate Similarity	NPC121121
0.7831	Intermediate Similarity	NPC153719
0.7831	Intermediate Similarity	NPC470610
0.7826	Intermediate Similarity	NPC24705
0.7826	Intermediate Similarity	NPC20822
0.7826	Intermediate Similarity	NPC56962
0.7816	Intermediate Similarity	NPC186594
0.7812	Intermediate Similarity	NPC274793
0.7802	Intermediate Similarity	NPC239938
0.7791	Intermediate Similarity	NPC43463
0.7789	Intermediate Similarity	NPC473065
0.7789	Intermediate Similarity	NPC241047
0.7789	Intermediate Similarity	NPC473064
0.7789	Intermediate Similarity	NPC17336
0.7789	Intermediate Similarity	NPC94582
0.7789	Intermediate Similarity	NPC473067
0.7789	Intermediate Similarity	NPC57964
0.7778	Intermediate Similarity	NPC235402
0.7778	Intermediate Similarity	NPC474756
0.7766	Intermediate Similarity	NPC311246
0.7766	Intermediate Similarity	NPC277774
0.7766	Intermediate Similarity	NPC167644
0.7765	Intermediate Similarity	NPC470145
0.7765	Intermediate Similarity	NPC136424
0.7755	Intermediate Similarity	NPC49532
0.7753	Intermediate Similarity	NPC478054
0.7742	Intermediate Similarity	NPC219937
0.7742	Intermediate Similarity	NPC123252
0.7742	Intermediate Similarity	NPC279329
0.7742	Intermediate Similarity	NPC194485
0.7742	Intermediate Similarity	NPC53890
0.7738	Intermediate Similarity	NPC48795
0.7738	Intermediate Similarity	NPC470151
0.7732	Intermediate Similarity	NPC300179
0.7732	Intermediate Similarity	NPC253995
0.7732	Intermediate Similarity	NPC102426
0.7727	Intermediate Similarity	NPC211049
0.7727	Intermediate Similarity	NPC473257
0.7727	Intermediate Similarity	NPC12933
0.7711	Intermediate Similarity	NPC470071
0.7711	Intermediate Similarity	NPC1340
0.7711	Intermediate Similarity	NPC252182
0.7711	Intermediate Similarity	NPC187471
0.7708	Intermediate Similarity	NPC471903
0.7708	Intermediate Similarity	NPC238796
0.7708	Intermediate Similarity	NPC142264
0.7708	Intermediate Similarity	NPC203434
0.7708	Intermediate Similarity	NPC476510
0.7708	Intermediate Similarity	NPC237071
0.77	Intermediate Similarity	NPC100078
0.7692	Intermediate Similarity	NPC471410
0.7692	Intermediate Similarity	NPC471411
0.7692	Intermediate Similarity	NPC474448
0.7684	Intermediate Similarity	NPC470423
0.7684	Intermediate Similarity	NPC477495
0.766	Intermediate Similarity	NPC59006
0.766	Intermediate Similarity	NPC5632
0.766	Intermediate Similarity	NPC130840

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 NPC5943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	3965
0.2-0.3	3307
0.3-0.4	804
0.4-0.5	327
0.5-0.6	222
0.6-0.7	93
0.7-0.8	4
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
0.747	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6928	Phase 2
0.7386	Intermediate Similarity	NPD6115	Approved
0.7386	Intermediate Similarity	NPD6118	Approved
0.7386	Intermediate Similarity	NPD6114	Approved
0.7386	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6116	Phase 1
0.7228	Intermediate Similarity	NPD1700	Approved
0.7216	Intermediate Similarity	NPD8171	Discontinued
0.7159	Intermediate Similarity	NPD6117	Approved
0.6964	Remote Similarity	NPD7516	Approved
0.6932	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7328	Approved
0.6875	Remote Similarity	NPD7327	Approved
0.6867	Remote Similarity	NPD371	Approved
0.6857	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3702	Approved
0.6782	Remote Similarity	NPD4787	Phase 1
0.6782	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6609	Remote Similarity	NPD8294	Approved
0.6609	Remote Similarity	NPD8377	Approved
0.6606	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8033	Approved
0.6538	Remote Similarity	NPD7638	Approved
0.6517	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5777	Approved
0.6517	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3703	Phase 2
0.6481	Remote Similarity	NPD6402	Approved
0.6481	Remote Similarity	NPD6675	Approved
0.6481	Remote Similarity	NPD5739	Approved
0.6481	Remote Similarity	NPD7128	Approved
0.6476	Remote Similarity	NPD7639	Approved
0.6476	Remote Similarity	NPD7640	Approved
0.6436	Remote Similarity	NPD8035	Phase 2
0.6436	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD7991	Discontinued
0.6404	Remote Similarity	NPD4245	Approved
0.6404	Remote Similarity	NPD4244	Approved
0.6372	Remote Similarity	NPD8133	Approved
0.6372	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD7524	Approved
0.6364	Remote Similarity	NPD6899	Approved
0.6355	Remote Similarity	NPD7632	Discontinued
0.6333	Remote Similarity	NPD7507	Approved
0.633	Remote Similarity	NPD6008	Approved
0.6327	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD7525	Registered
0.6311	Remote Similarity	NPD7319	Approved
0.6306	Remote Similarity	NPD6373	Approved
0.6306	Remote Similarity	NPD6372	Approved
0.6303	Remote Similarity	NPD7604	Phase 2
0.6292	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3698	Phase 2
0.6283	Remote Similarity	NPD8297	Approved
0.6281	Remote Similarity	NPD7078	Approved
0.6273	Remote Similarity	NPD5697	Approved
0.6273	Remote Similarity	NPD5701	Approved
0.6271	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD7492	Approved
0.6224	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6616	Approved
0.6195	Remote Similarity	NPD6649	Approved
0.6195	Remote Similarity	NPD6847	Approved
0.6195	Remote Similarity	NPD6650	Approved
0.6195	Remote Similarity	NPD6869	Approved
0.6195	Remote Similarity	NPD6617	Approved
0.6195	Remote Similarity	NPD8130	Phase 1
0.6186	Remote Similarity	NPD6054	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.618	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5360	Phase 3
0.6161	Remote Similarity	NPD6014	Approved
0.6161	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6012	Approved
0.6161	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6081	Approved
0.6148	Remote Similarity	NPD8293	Discontinued
0.614	Remote Similarity	NPD6882	Approved
0.6132	Remote Similarity	NPD6084	Phase 2
0.6132	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD6412	Phase 2
0.6122	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD3669	Approved
0.6122	Remote Similarity	NPD6695	Phase 3
0.6121	Remote Similarity	NPD6940	Discontinued
0.6111	Remote Similarity	NPD4159	Approved
0.6111	Remote Similarity	NPD5344	Discontinued
0.6098	Remote Similarity	NPD7736	Approved
0.6095	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6370	Approved
0.6071	Remote Similarity	NPD6011	Approved
0.6068	Remote Similarity	NPD6009	Approved
0.6058	Remote Similarity	NPD6399	Phase 3
0.6053	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4789	Approved
0.6022	Remote Similarity	NPD1811	Approved
0.6022	Remote Similarity	NPD1810	Approved
0.6019	Remote Similarity	NPD8418	Phase 2
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD5983	Phase 2
0.5982	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4755	Approved
0.5965	Remote Similarity	NPD4634	Approved
0.5962	Remote Similarity	NPD7637	Suspended
0.5955	Remote Similarity	NPD4224	Phase 2
0.595	Remote Similarity	NPD5988	Approved
0.5946	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6336	Discontinued
0.5932	Remote Similarity	NPD7115	Discovery
0.5922	Remote Similarity	NPD6051	Approved
0.5905	Remote Similarity	NPD4202	Approved
0.5882	Remote Similarity	NPD7750	Discontinued
0.5872	Remote Similarity	NPD4700	Approved
0.5872	Remote Similarity	NPD5286	Approved
0.5872	Remote Similarity	NPD4696	Approved
0.5872	Remote Similarity	NPD5285	Approved
0.5868	Remote Similarity	NPD6921	Approved
0.5862	Remote Similarity	NPD6053	Discontinued
0.5847	Remote Similarity	NPD6274	Approved
0.5833	Remote Similarity	NPD7100	Approved
0.5833	Remote Similarity	NPD7101	Approved
0.5825	Remote Similarity	NPD6903	Approved
0.5816	Remote Similarity	NPD6931	Approved
0.5816	Remote Similarity	NPD4748	Discontinued
0.5816	Remote Similarity	NPD6930	Phase 2
0.5814	Remote Similarity	NPD3198	Approved
0.5806	Remote Similarity	NPD4758	Discontinued
0.58	Remote Similarity	NPD4788	Approved
0.5794	Remote Similarity	NPD5695	Phase 3
0.578	Remote Similarity	NPD4225	Approved
0.578	Remote Similarity	NPD5696	Approved
0.5773	Remote Similarity	NPD5364	Discontinued
0.5773	Remote Similarity	NPD3671	Phase 1
0.5773	Remote Similarity	NPD4238	Approved
0.5773	Remote Similarity	NPD4802	Phase 2
0.5766	Remote Similarity	NPD5225	Approved
0.5766	Remote Similarity	NPD5211	Phase 2
0.5766	Remote Similarity	NPD4633	Approved
0.5766	Remote Similarity	NPD5224	Approved
0.5766	Remote Similarity	NPD5226	Approved
0.575	Remote Similarity	NPD6335	Approved
0.5738	Remote Similarity	NPD6909	Approved
0.5738	Remote Similarity	NPD6908	Approved
0.5729	Remote Similarity	NPD6933	Approved
0.5729	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6648	Approved
0.5714	Remote Similarity	NPD6700	Approved
0.5714	Remote Similarity	NPD5175	Approved
0.5714	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD6929	Approved
0.5714	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6033	Approved
0.5702	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6001	Approved
0.5699	Remote Similarity	NPD2686	Approved
0.5699	Remote Similarity	NPD2687	Approved
0.5699	Remote Similarity	NPD2254	Approved
0.5676	Remote Similarity	NPD5223	Approved
0.567	Remote Similarity	NPD6932	Approved
0.5667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6317	Approved
0.5664	Remote Similarity	NPD5141	Approved
0.566	Remote Similarity	NPD7087	Discontinued
0.566	Remote Similarity	NPD6702	Approved
0.566	Remote Similarity	NPD6703	Approved
0.5652	Remote Similarity	NPD6686	Approved
0.5652	Remote Similarity	NPD6705	Phase 1
0.5645	Remote Similarity	NPD6067	Discontinued
0.5631	Remote Similarity	NPD7334	Approved
0.5631	Remote Similarity	NPD7146	Approved
0.5631	Remote Similarity	NPD5330	Approved
0.5631	Remote Similarity	NPD6409	Approved
0.5631	Remote Similarity	NPD8308	Discontinued
0.5631	Remote Similarity	NPD7521	Approved
0.5631	Remote Similarity	NPD6684	Approved
0.5625	Remote Similarity	NPD7339	Approved
0.5625	Remote Similarity	NPD6942	Approved
0.562	Remote Similarity	NPD6314	Approved
0.562	Remote Similarity	NPD6313	Approved
0.5619	Remote Similarity	NPD5328	Approved
0.5619	Remote Similarity	NPD4753	Phase 2

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