NPASS Compound

Structure

NPC174051 OpenBabel07101719512D 34 38 0 0 1 0 0 0 0 0999 V2000 2.8963 0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8058 -1.8576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5979 -0.8795 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 1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 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 1.2024 -1.0827 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 -0.9781 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 2.5873 0.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 1 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 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 -0.7044 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2075 -1.0134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1857 -0.8055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8548 -1.5486 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 0.5000 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 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4947 0.1456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5458 -2.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4644 -1.6825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 0 0 0 0 17 1 1 1 0 0 0 17 18 1 0 0 0 0 18 29 1 6 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 1 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 17 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 25 1 6 0 0 0 24 34 1 0 0 0 0 25 27 1 0 0 0 0 25 32 1 1 0 0 0 27 33 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.671
LogD:	4.643
LogS:	-4.631
# Rotatable Bonds:	4
TPSA:	70.06
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	5.178
Fsp3:	0.9
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:	-4.872
MDCK Permeability:	1.2685865840467159e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.244
Plasma Protein Binding (PPB):	91.99638366699219%
Volume Distribution (VD):	1.095
Pgp-substrate:	3.606229305267334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.521
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.67
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	6.666
Half-life (T1/2):	0.219

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.421
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.815
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.072
Carcinogencity:	0.18
Eye Corrosion:	0.006
Eye Irritation:	0.017
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC174051

Natural Product ID:	NPC174051
*Common Name:**	Toonapubesin B
IUPAC Name:	(5R,9R,10R,13S,14S,17S)-17-[(1R)-1-[(2S,3S)-3-[(1R)-1,2-dihydroxy-2-methylpropyl]oxiran-2-yl]ethyl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	ADFOHQSVHIRDGE-OMVHEGIWSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-17(23-24(34-23)25(32)27(4,5)33)18-11-15-30(8)20-9-10-21-26(2,3)22(31)13-14-28(21,6)19(20)12-16-29(18,30)7/h9,17-19,21,23-25,32-33H,10-16H2,1-8H3/t17-,18+,19+,21+,23+,24-,25-,28-,29+,30-/m1/s1
SMILES:	C[C@H]([C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@H]3CC[C@@]12C)[C@H]1[C@H]([C@H](C(C)(C)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581398
PubChem CID:	56641019
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32927.1	Dysoxylum mollissimum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25781655]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI	<	50.0	%	PMID[458522]
NPT168	Cell Line	P388	Mus musculus	GI	<	50.0	%	PMID[458522]
NPT116	Cell Line	HL-60	Homo sapiens	GI	<	50.0	%	PMID[458522]

☑ 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 NPC174051 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	184
0.1-0.2	1134
0.2-0.3	5017
0.3-0.4	14009
0.4-0.5	7842
0.5-0.6	5665
0.6-0.7	6548
0.7-0.8	2137
0.8-0.85	137
0.85-0.9	14
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67831
0.977	High Similarity	NPC262870
0.9425	High Similarity	NPC470417
0.931	High Similarity	NPC90652
0.9043	High Similarity	NPC167974
0.8947	High Similarity	NPC476897
0.8913	High Similarity	NPC318332
0.8889	High Similarity	NPC32830
0.8876	High Similarity	NPC469322
0.8854	High Similarity	NPC473928
0.8791	High Similarity	NPC171441
0.8778	High Similarity	NPC44181
0.8764	High Similarity	NPC473168
0.8673	High Similarity	NPC75531
0.8673	High Similarity	NPC149124
0.8673	High Similarity	NPC121566
0.8673	High Similarity	NPC100955
0.8602	High Similarity	NPC274046
0.8602	High Similarity	NPC198074
0.8586	High Similarity	NPC63023
0.8586	High Similarity	NPC95243
0.8571	High Similarity	NPC255176
0.8556	High Similarity	NPC89077
0.8556	High Similarity	NPC125399
0.8539	High Similarity	NPC214043
0.8539	High Similarity	NPC221758
0.8539	High Similarity	NPC82902
0.8539	High Similarity	NPC59453
0.8539	High Similarity	NPC85774
0.85	High Similarity	NPC144459
0.8495	Intermediate Similarity	NPC154101
0.8478	Intermediate Similarity	NPC474245
0.8478	Intermediate Similarity	NPC476733
0.8478	Intermediate Similarity	NPC215029
0.8478	Intermediate Similarity	NPC1015
0.8478	Intermediate Similarity	NPC31985
0.8462	Intermediate Similarity	NPC474174
0.8462	Intermediate Similarity	NPC251808
0.8462	Intermediate Similarity	NPC317590
0.8444	Intermediate Similarity	NPC474218
0.8444	Intermediate Similarity	NPC471224
0.8427	Intermediate Similarity	NPC86370
0.8387	Intermediate Similarity	NPC320026
0.8384	Intermediate Similarity	NPC239716
0.8367	Intermediate Similarity	NPC473174
0.8365	Intermediate Similarity	NPC317210
0.8352	Intermediate Similarity	NPC474732
0.8352	Intermediate Similarity	NPC145879
0.8352	Intermediate Similarity	NPC31564
0.8352	Intermediate Similarity	NPC51014
0.8352	Intermediate Similarity	NPC469994
0.8352	Intermediate Similarity	NPC474733
0.8352	Intermediate Similarity	NPC474778
0.8333	Intermediate Similarity	NPC473246
0.8316	Intermediate Similarity	NPC473172
0.8315	Intermediate Similarity	NPC151519
0.8315	Intermediate Similarity	NPC212083
0.83	Intermediate Similarity	NPC471293
0.8298	Intermediate Similarity	NPC473166
0.8298	Intermediate Similarity	NPC189520
0.8298	Intermediate Similarity	NPC155304
0.8283	Intermediate Similarity	NPC473163
0.828	Intermediate Similarity	NPC475921
0.828	Intermediate Similarity	NPC326627
0.828	Intermediate Similarity	NPC76879
0.828	Intermediate Similarity	NPC2983
0.828	Intermediate Similarity	NPC310010
0.828	Intermediate Similarity	NPC474704
0.828	Intermediate Similarity	NPC477943
0.828	Intermediate Similarity	NPC474570
0.8265	Intermediate Similarity	NPC83709
0.8261	Intermediate Similarity	NPC138756
0.8261	Intermediate Similarity	NPC475740
0.8261	Intermediate Similarity	NPC96496
0.8261	Intermediate Similarity	NPC99909
0.8261	Intermediate Similarity	NPC58063
0.8252	Intermediate Similarity	NPC52241
0.8252	Intermediate Similarity	NPC475317
0.8252	Intermediate Similarity	NPC154856
0.8247	Intermediate Similarity	NPC57416
0.8247	Intermediate Similarity	NPC107243
0.8242	Intermediate Similarity	NPC474083
0.8242	Intermediate Similarity	NPC474349
0.8242	Intermediate Similarity	NPC474189
0.8242	Intermediate Similarity	NPC469948
0.8235	Intermediate Similarity	NPC258323
0.8229	Intermediate Similarity	NPC473170
0.8229	Intermediate Similarity	NPC469599
0.8218	Intermediate Similarity	NPC162033
0.8211	Intermediate Similarity	NPC475255
0.8211	Intermediate Similarity	NPC474807
0.8211	Intermediate Similarity	NPC474736
0.82	Intermediate Similarity	NPC117185
0.8191	Intermediate Similarity	NPC471896
0.8182	Intermediate Similarity	NPC215843
0.8172	Intermediate Similarity	NPC328313
0.8172	Intermediate Similarity	NPC193360
0.8161	Intermediate Similarity	NPC325946
0.8155	Intermediate Similarity	NPC284828
0.8155	Intermediate Similarity	NPC472216
0.8155	Intermediate Similarity	NPC246205
0.8155	Intermediate Similarity	NPC173905
0.8155	Intermediate Similarity	NPC5475
0.8152	Intermediate Similarity	NPC155011
0.8152	Intermediate Similarity	NPC324063
0.8144	Intermediate Similarity	NPC49371
0.8144	Intermediate Similarity	NPC471777
0.8144	Intermediate Similarity	NPC473164
0.8137	Intermediate Similarity	NPC59530
0.8132	Intermediate Similarity	NPC227064
0.8132	Intermediate Similarity	NPC161423
0.8132	Intermediate Similarity	NPC237712
0.8132	Intermediate Similarity	NPC329043
0.8132	Intermediate Similarity	NPC321187
0.8132	Intermediate Similarity	NPC58841
0.8125	Intermediate Similarity	NPC8993
0.8125	Intermediate Similarity	NPC111015
0.8119	Intermediate Similarity	NPC255309
0.8119	Intermediate Similarity	NPC223741
0.8111	Intermediate Similarity	NPC145143
0.8111	Intermediate Similarity	NPC30166
0.8105	Intermediate Similarity	NPC210268
0.8105	Intermediate Similarity	NPC19114
0.8105	Intermediate Similarity	NPC473998
0.8105	Intermediate Similarity	NPC475806
0.81	Intermediate Similarity	NPC22388
0.81	Intermediate Similarity	NPC185530
0.8095	Intermediate Similarity	NPC210420
0.8095	Intermediate Similarity	NPC474265
0.8095	Intermediate Similarity	NPC207251
0.8095	Intermediate Similarity	NPC130427
0.809	Intermediate Similarity	NPC472478
0.8085	Intermediate Similarity	NPC54689
0.8085	Intermediate Similarity	NPC473999
0.8085	Intermediate Similarity	NPC250592
0.8085	Intermediate Similarity	NPC186688
0.8085	Intermediate Similarity	NPC268406
0.8085	Intermediate Similarity	NPC26959
0.8085	Intermediate Similarity	NPC77263
0.8085	Intermediate Similarity	NPC309603
0.8077	Intermediate Similarity	NPC76084
0.8077	Intermediate Similarity	NPC101450
0.8068	Intermediate Similarity	NPC82635
0.8065	Intermediate Similarity	NPC469317
0.8065	Intermediate Similarity	NPC241875
0.8065	Intermediate Similarity	NPC469314
0.8065	Intermediate Similarity	NPC474684
0.8065	Intermediate Similarity	NPC167877
0.8065	Intermediate Similarity	NPC142361
0.8065	Intermediate Similarity	NPC93778
0.8061	Intermediate Similarity	NPC475894
0.8061	Intermediate Similarity	NPC210337
0.8061	Intermediate Similarity	NPC272451
0.8061	Intermediate Similarity	NPC18509
0.8058	Intermediate Similarity	NPC295389
0.8058	Intermediate Similarity	NPC472219
0.8058	Intermediate Similarity	NPC472218
0.8058	Intermediate Similarity	NPC472217
0.8056	Intermediate Similarity	NPC50774
0.8056	Intermediate Similarity	NPC709
0.8043	Intermediate Similarity	NPC470574
0.8043	Intermediate Similarity	NPC202868
0.8041	Intermediate Similarity	NPC473415
0.8041	Intermediate Similarity	NPC279974
0.8041	Intermediate Similarity	NPC469329
0.8041	Intermediate Similarity	NPC30677
0.8041	Intermediate Similarity	NPC37787
0.8041	Intermediate Similarity	NPC180557
0.8039	Intermediate Similarity	NPC210178
0.8039	Intermediate Similarity	NPC96377
0.8022	Intermediate Similarity	NPC470047
0.8022	Intermediate Similarity	NPC470046
0.8022	Intermediate Similarity	NPC476082
0.8022	Intermediate Similarity	NPC472744
0.8022	Intermediate Similarity	NPC278648
0.8021	Intermediate Similarity	NPC472942
0.8021	Intermediate Similarity	NPC470375
0.8021	Intermediate Similarity	NPC152897
0.8021	Intermediate Similarity	NPC141497
0.8021	Intermediate Similarity	NPC66429
0.8021	Intermediate Similarity	NPC470376
0.8021	Intermediate Similarity	NPC470224
0.8021	Intermediate Similarity	NPC98193
0.8021	Intermediate Similarity	NPC472930
0.8021	Intermediate Similarity	NPC233118
0.8021	Intermediate Similarity	NPC243866
0.8021	Intermediate Similarity	NPC107674
0.8021	Intermediate Similarity	NPC170220
0.802	Intermediate Similarity	NPC26478
0.802	Intermediate Similarity	NPC191892
0.8019	Intermediate Similarity	NPC178981
0.8019	Intermediate Similarity	NPC477944
0.8	Intermediate Similarity	NPC111585
0.8	Intermediate Similarity	NPC48010
0.8	Intermediate Similarity	NPC147066
0.8	Intermediate Similarity	NPC148414
0.8	Intermediate Similarity	NPC289213
0.8	Intermediate Similarity	NPC136801
0.8	Intermediate Similarity	NPC175628
0.8	Intermediate Similarity	NPC474327

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 NPC174051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1432
0.2-0.3	4115
0.3-0.4	2362
0.4-0.5	590
0.5-0.6	184
0.6-0.7	154
0.7-0.8	148
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8539	High Similarity	NPD4786	Approved
0.8404	Intermediate Similarity	NPD6399	Phase 3
0.8315	Intermediate Similarity	NPD3667	Approved
0.828	Intermediate Similarity	NPD4753	Phase 2
0.8247	Intermediate Similarity	NPD6084	Phase 2
0.8247	Intermediate Similarity	NPD6083	Phase 2
0.8137	Intermediate Similarity	NPD6412	Phase 2
0.8132	Intermediate Similarity	NPD3665	Phase 1
0.8132	Intermediate Similarity	NPD3133	Approved
0.8132	Intermediate Similarity	NPD3666	Approved
0.8085	Intermediate Similarity	NPD5328	Approved
0.8061	Intermediate Similarity	NPD4755	Approved
0.8039	Intermediate Similarity	NPD7128	Approved
0.8039	Intermediate Similarity	NPD5739	Approved
0.8039	Intermediate Similarity	NPD6675	Approved
0.8039	Intermediate Similarity	NPD6402	Approved
0.8021	Intermediate Similarity	NPD4202	Approved
0.7963	Intermediate Similarity	NPD7115	Discovery
0.7957	Intermediate Similarity	NPD3618	Phase 1
0.7925	Intermediate Similarity	NPD8297	Approved
0.7917	Intermediate Similarity	NPD6079	Approved
0.7912	Intermediate Similarity	NPD4223	Phase 3
0.7912	Intermediate Similarity	NPD4221	Approved
0.79	Intermediate Similarity	NPD5286	Approved
0.79	Intermediate Similarity	NPD4700	Approved
0.79	Intermediate Similarity	NPD4696	Approved
0.79	Intermediate Similarity	NPD5285	Approved
0.7885	Intermediate Similarity	NPD6881	Approved
0.7885	Intermediate Similarity	NPD6899	Approved
0.7885	Intermediate Similarity	NPD7320	Approved
0.7857	Intermediate Similarity	NPD5695	Phase 3
0.7857	Intermediate Similarity	NPD5210	Approved
0.7857	Intermediate Similarity	NPD4629	Approved
0.7849	Intermediate Similarity	NPD5329	Approved
0.781	Intermediate Similarity	NPD6373	Approved
0.781	Intermediate Similarity	NPD6372	Approved
0.78	Intermediate Similarity	NPD5696	Approved
0.7789	Intermediate Similarity	NPD5737	Approved
0.7789	Intermediate Similarity	NPD6672	Approved
0.7788	Intermediate Similarity	NPD5697	Approved
0.7788	Intermediate Similarity	NPD5701	Approved
0.7766	Intermediate Similarity	NPD5330	Approved
0.7766	Intermediate Similarity	NPD5279	Phase 3
0.7766	Intermediate Similarity	NPD7521	Approved
0.7766	Intermediate Similarity	NPD7334	Approved
0.7766	Intermediate Similarity	NPD6684	Approved
0.7766	Intermediate Similarity	NPD6409	Approved
0.7766	Intermediate Similarity	NPD7146	Approved
0.7745	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD4633	Approved
0.7745	Intermediate Similarity	NPD5224	Approved
0.7745	Intermediate Similarity	NPD5226	Approved
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7742	Intermediate Similarity	NPD3668	Phase 3
0.7742	Intermediate Similarity	NPD4197	Approved
0.7736	Intermediate Similarity	NPD6883	Approved
0.7736	Intermediate Similarity	NPD7102	Approved
0.7736	Intermediate Similarity	NPD7290	Approved
0.7692	Intermediate Similarity	NPD7525	Registered
0.767	Intermediate Similarity	NPD5174	Approved
0.767	Intermediate Similarity	NPD5175	Approved
0.7664	Intermediate Similarity	NPD6847	Approved
0.7664	Intermediate Similarity	NPD6649	Approved
0.7664	Intermediate Similarity	NPD8130	Phase 1
0.7664	Intermediate Similarity	NPD6650	Approved
0.7664	Intermediate Similarity	NPD6617	Approved
0.7664	Intermediate Similarity	NPD6869	Approved
0.7647	Intermediate Similarity	NPD5223	Approved
0.7642	Intermediate Similarity	NPD6014	Approved
0.7642	Intermediate Similarity	NPD6012	Approved
0.7642	Intermediate Similarity	NPD6013	Approved
0.7634	Intermediate Similarity	NPD4788	Approved
0.7604	Intermediate Similarity	NPD6903	Approved
0.7604	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD4697	Phase 3
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD5141	Approved
0.7593	Intermediate Similarity	NPD6882	Approved
0.7579	Intermediate Similarity	NPD4693	Phase 3
0.7579	Intermediate Similarity	NPD5205	Approved
0.7579	Intermediate Similarity	NPD4138	Approved
0.7579	Intermediate Similarity	NPD4688	Approved
0.7579	Intermediate Similarity	NPD6098	Approved
0.7579	Intermediate Similarity	NPD4690	Approved
0.7579	Intermediate Similarity	NPD4689	Approved
0.757	Intermediate Similarity	NPD4634	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7528	Intermediate Similarity	NPD7339	Approved
0.7528	Intermediate Similarity	NPD6942	Approved
0.7526	Intermediate Similarity	NPD6673	Approved
0.7526	Intermediate Similarity	NPD6080	Approved
0.7526	Intermediate Similarity	NPD6904	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7524	Intermediate Similarity	NPD4767	Approved
0.7524	Intermediate Similarity	NPD4768	Approved
0.7523	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD7524	Approved
0.7444	Intermediate Similarity	NPD6933	Approved
0.7434	Intermediate Similarity	NPD6054	Approved
0.7434	Intermediate Similarity	NPD6319	Approved
0.7434	Intermediate Similarity	NPD6059	Approved
0.74	Intermediate Similarity	NPD7748	Approved
0.7396	Intermediate Similarity	NPD4694	Approved
0.7396	Intermediate Similarity	NPD5280	Approved
0.7396	Intermediate Similarity	NPD5690	Phase 2
0.7396	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD5128	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD5281	Approved
0.7374	Intermediate Similarity	NPD7515	Phase 2
0.7374	Intermediate Similarity	NPD5284	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6008	Approved
0.7353	Intermediate Similarity	NPD7902	Approved
0.7315	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6370	Approved
0.7292	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3617	Approved
0.7263	Intermediate Similarity	NPD6695	Phase 3
0.7253	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5248	Approved
0.7245	Intermediate Similarity	NPD5208	Approved
0.7241	Intermediate Similarity	NPD7604	Phase 2
0.7234	Intermediate Similarity	NPD4692	Approved
0.7234	Intermediate Similarity	NPD4139	Approved
0.7232	Intermediate Similarity	NPD6274	Approved
0.7222	Intermediate Similarity	NPD6686	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.7217	Intermediate Similarity	NPD6016	Approved
0.7217	Intermediate Similarity	NPD6015	Approved
0.7204	Intermediate Similarity	NPD4195	Approved
0.72	Intermediate Similarity	NPD6050	Approved
0.72	Intermediate Similarity	NPD5693	Phase 1
0.7193	Intermediate Similarity	NPD7101	Approved
0.7193	Intermediate Similarity	NPD7100	Approved
0.7191	Intermediate Similarity	NPD4243	Approved
0.7182	Intermediate Similarity	NPD5217	Approved
0.7182	Intermediate Similarity	NPD5216	Approved
0.7182	Intermediate Similarity	NPD5215	Approved
0.7179	Intermediate Similarity	NPD7492	Approved
0.7168	Intermediate Similarity	NPD6009	Approved
0.7155	Intermediate Similarity	NPD5988	Approved
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7119	Intermediate Similarity	NPD6616	Approved
0.7115	Intermediate Similarity	NPD7638	Approved
0.7105	Intermediate Similarity	NPD6335	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5135	Approved
0.7079	Intermediate Similarity	NPD4747	Approved
0.7069	Intermediate Similarity	NPD6909	Approved
0.7069	Intermediate Similarity	NPD5983	Phase 2
0.7069	Intermediate Similarity	NPD6908	Approved
0.7059	Intermediate Similarity	NPD6001	Approved
0.7059	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7900	Approved
0.7059	Intermediate Similarity	NPD8293	Discontinued
0.7059	Intermediate Similarity	NPD7078	Approved
0.7048	Intermediate Similarity	NPD7639	Approved
0.7048	Intermediate Similarity	NPD7640	Approved
0.7043	Intermediate Similarity	NPD4522	Approved
0.7041	Intermediate Similarity	NPD4623	Approved
0.7041	Intermediate Similarity	NPD4519	Discontinued
0.7033	Intermediate Similarity	NPD4784	Approved
0.7033	Intermediate Similarity	NPD4785	Approved
0.703	Intermediate Similarity	NPD5694	Approved
0.703	Intermediate Similarity	NPD6411	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7018	Intermediate Similarity	NPD6317	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6435	Approved
0.6975	Remote Similarity	NPD7507	Approved
0.6975	Remote Similarity	NPD6336	Discontinued
0.697	Remote Similarity	NPD7750	Discontinued
0.6966	Remote Similarity	NPD4137	Phase 3
0.6961	Remote Similarity	NPD5133	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6947	Remote Similarity	NPD6931	Approved
0.6947	Remote Similarity	NPD6930	Phase 2
0.6937	Remote Similarity	NPD5955	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data