NPASS Compound

Structure

NPC84383 OpenBabel07101719192D 45 49 0 0 1 0 0 0 0 0999 V2000 6.9282 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3096 5.2471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5175 4.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 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 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 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 -0.8660 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 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 1 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 -5.5665 4.5780 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 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 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 -4.8973 5.3212 0.0000 O 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 1 9 1 0 0 0 0 3 37 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 38 1 0 0 0 0 7 39 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 31 1 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 0 0 0 0 25 37 1 0 0 0 0 26 40 1 0 0 0 0 27 41 1 0 0 0 0 28 29 1 0 0 0 0 28 39 1 0 0 0 0 30 41 1 0 0 0 0 30 42 1 0 0 0 0 31 2 1 1 0 0 0 31 32 1 0 0 0 0 32 39 1 6 0 0 0 33 38 1 0 0 0 0 33 41 1 6 0 0 0 34 40 1 1 0 0 0 34 42 1 0 0 0 0 35 38 1 0 0 0 0 35 45 1 6 0 0 0 36 43 2 0 0 0 0 36 45 1 0 0 0 0 37 44 1 0 0 0 0 39 40 1 6 0 0 0 40 8 1 1 0 0 0 41 42 1 1 0 0 0 42 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.55
Volume:	713.303
LogP:	10.869
LogD:	6.476
LogS:	-7.295
# Rotatable Bonds:	16
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.112
Synthetic Accessibility Score:	5.618
Fsp3:	0.929
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.986
MDCK Permeability:	9.904486432787962e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.978
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	95.99390411376953%
Volume Distribution (VD):	1.391
Pgp-substrate:	1.5286827087402344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.801
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	4.683
Half-life (T1/2):	0.029

ADMET: Toxicity

hERG Blockers:	0.897
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.0
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.972
Carcinogencity:	0.031
Eye Corrosion:	0.124
Eye Irritation:	0.167
Respiratory Toxicity:	0.614

Download Data

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

Natural Product: NPC84383

Natural Product ID:	NPC84383
*Common Name:**	BIRNPJCAAKNGGH-JNUUMGRKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BIRNPJCAAKNGGH-JNUUMGRKSA-N
Standard InCHI:	InChI=1S/C42H72O3/c1-9-10-11-12-13-14-15-16-17-20-36(43)45-35-24-27-41-30-42(41)29-28-39(7)32(31(2)19-18-25-37(3,4)44)23-26-40(39,8)34(42)22-21-33(41)38(35,5)6/h18,25,31-35,44H,9-17,19-24,26-30H2,1-8H3/b25-18+/t31-,32-,33+,34+,35+,39-,40+,41-,42+/m1/s1
SMILES:	CCCCCCCCCCCC(=O)O[C@H]1CC[C@@]23C[C@@]43CC[C@]3(C)[C@H](CC[C@@]3(C)[C@@H]4CC[C@H]2C1(C)C)[C@H](C)C/C=C/C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451759
PubChem CID:	44566686
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128.0	ug.mL-1	PMID[464560]

☑ 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 NPC84383 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	187
0.1-0.2	1256
0.2-0.3	4823
0.3-0.4	14758
0.4-0.5	7705
0.5-0.6	6176
0.6-0.7	5718
0.7-0.8	1957
0.8-0.85	100
0.85-0.9	16
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.883	High Similarity	NPC327788
0.8723	High Similarity	NPC279974
0.8696	High Similarity	NPC471896
0.8673	High Similarity	NPC222153
0.8632	High Similarity	NPC160056
0.8587	High Similarity	NPC128496
0.8586	High Similarity	NPC201763
0.8539	High Similarity	NPC139206
0.8495	Intermediate Similarity	NPC175628
0.8495	Intermediate Similarity	NPC148414
0.8495	Intermediate Similarity	NPC111585
0.8485	Intermediate Similarity	NPC180204
0.8462	Intermediate Similarity	NPC264127
0.8454	Intermediate Similarity	NPC119036
0.8431	Intermediate Similarity	NPC257082
0.8416	Intermediate Similarity	NPC263729
0.8404	Intermediate Similarity	NPC26888
0.8404	Intermediate Similarity	NPC177641
0.8404	Intermediate Similarity	NPC74296
0.8404	Intermediate Similarity	NPC110923
0.8404	Intermediate Similarity	NPC470113
0.8387	Intermediate Similarity	NPC474889
0.8384	Intermediate Similarity	NPC320447
0.837	Intermediate Similarity	NPC142361
0.837	Intermediate Similarity	NPC128644
0.837	Intermediate Similarity	NPC474684
0.8367	Intermediate Similarity	NPC201406
0.8367	Intermediate Similarity	NPC266955
0.8352	Intermediate Similarity	NPC283733
0.8333	Intermediate Similarity	NPC163216
0.8333	Intermediate Similarity	NPC472219
0.8333	Intermediate Similarity	NPC82623
0.8333	Intermediate Similarity	NPC472217
0.8333	Intermediate Similarity	NPC476174
0.8333	Intermediate Similarity	NPC293052
0.8333	Intermediate Similarity	NPC472218
0.8316	Intermediate Similarity	NPC476304
0.8316	Intermediate Similarity	NPC38232
0.8316	Intermediate Similarity	NPC470224
0.83	Intermediate Similarity	NPC475526
0.83	Intermediate Similarity	NPC329345
0.83	Intermediate Similarity	NPC476237
0.83	Intermediate Similarity	NPC112009
0.83	Intermediate Similarity	NPC473283
0.83	Intermediate Similarity	NPC72151
0.8298	Intermediate Similarity	NPC469400
0.8283	Intermediate Similarity	NPC115899
0.8283	Intermediate Similarity	NPC118174
0.8283	Intermediate Similarity	NPC477053
0.8283	Intermediate Similarity	NPC477051
0.8283	Intermediate Similarity	NPC477052
0.8283	Intermediate Similarity	NPC476897
0.828	Intermediate Similarity	NPC472220
0.828	Intermediate Similarity	NPC4309
0.828	Intermediate Similarity	NPC97884
0.8265	Intermediate Similarity	NPC234617
0.8265	Intermediate Similarity	NPC124703
0.8265	Intermediate Similarity	NPC98868
0.8261	Intermediate Similarity	NPC325594
0.8252	Intermediate Similarity	NPC285298
0.8247	Intermediate Similarity	NPC54248
0.8247	Intermediate Similarity	NPC276103
0.8242	Intermediate Similarity	NPC476038
0.8242	Intermediate Similarity	NPC194937
0.8242	Intermediate Similarity	NPC475509
0.8229	Intermediate Similarity	NPC159410
0.8229	Intermediate Similarity	NPC469406
0.8229	Intermediate Similarity	NPC476186
0.8211	Intermediate Similarity	NPC475806
0.82	Intermediate Similarity	NPC477054
0.8191	Intermediate Similarity	NPC66344
0.8191	Intermediate Similarity	NPC475921
0.8191	Intermediate Similarity	NPC474704
0.8182	Intermediate Similarity	NPC476303
0.8182	Intermediate Similarity	NPC470074
0.8173	Intermediate Similarity	NPC16270
0.8172	Intermediate Similarity	NPC233836
0.8172	Intermediate Similarity	NPC159046
0.8172	Intermediate Similarity	NPC187376
0.8163	Intermediate Similarity	NPC107243
0.8152	Intermediate Similarity	NPC98270
0.8152	Intermediate Similarity	NPC269638
0.8152	Intermediate Similarity	NPC474971
0.8144	Intermediate Similarity	NPC33473
0.8144	Intermediate Similarity	NPC290481
0.8132	Intermediate Similarity	NPC134481
0.8132	Intermediate Similarity	NPC471037
0.8125	Intermediate Similarity	NPC477855
0.8119	Intermediate Similarity	NPC36688
0.8105	Intermediate Similarity	NPC113989
0.8105	Intermediate Similarity	NPC120840
0.81	Intermediate Similarity	NPC235142
0.81	Intermediate Similarity	NPC75941
0.809	Intermediate Similarity	NPC47808
0.8085	Intermediate Similarity	NPC117122
0.8085	Intermediate Similarity	NPC16377
0.8085	Intermediate Similarity	NPC146937
0.8085	Intermediate Similarity	NPC193360
0.8081	Intermediate Similarity	NPC477854
0.8077	Intermediate Similarity	NPC472216
0.8077	Intermediate Similarity	NPC284828
0.8077	Intermediate Similarity	NPC173905
0.8077	Intermediate Similarity	NPC5475
0.8065	Intermediate Similarity	NPC12774
0.8065	Intermediate Similarity	NPC28252
0.8065	Intermediate Similarity	NPC82979
0.8065	Intermediate Similarity	NPC91525
0.8065	Intermediate Similarity	NPC70661
0.8065	Intermediate Similarity	NPC9892
0.8065	Intermediate Similarity	NPC329943
0.8065	Intermediate Similarity	NPC10005
0.8065	Intermediate Similarity	NPC155011
0.8065	Intermediate Similarity	NPC73038
0.8065	Intermediate Similarity	NPC55309
0.8061	Intermediate Similarity	NPC250757
0.8061	Intermediate Similarity	NPC235053
0.8061	Intermediate Similarity	NPC301534
0.8061	Intermediate Similarity	NPC322063
0.8061	Intermediate Similarity	NPC29152
0.8061	Intermediate Similarity	NPC195366
0.8061	Intermediate Similarity	NPC307164
0.8061	Intermediate Similarity	NPC114743
0.8058	Intermediate Similarity	NPC473284
0.8058	Intermediate Similarity	NPC131665
0.8058	Intermediate Similarity	NPC255387
0.8043	Intermediate Similarity	NPC165064
0.8043	Intermediate Similarity	NPC306951
0.8041	Intermediate Similarity	NPC60692
0.8041	Intermediate Similarity	NPC292793
0.8041	Intermediate Similarity	NPC201725
0.8041	Intermediate Similarity	NPC8993
0.8022	Intermediate Similarity	NPC218616
0.8022	Intermediate Similarity	NPC296701
0.8021	Intermediate Similarity	NPC470590
0.8021	Intermediate Similarity	NPC49420
0.8021	Intermediate Similarity	NPC160506
0.8021	Intermediate Similarity	NPC471901
0.8021	Intermediate Similarity	NPC285184
0.8021	Intermediate Similarity	NPC77099
0.8021	Intermediate Similarity	NPC475416
0.8021	Intermediate Similarity	NPC189520
0.8021	Intermediate Similarity	NPC60755
0.802	Intermediate Similarity	NPC469316
0.802	Intermediate Similarity	NPC136289
0.802	Intermediate Similarity	NPC32577
0.802	Intermediate Similarity	NPC155332
0.802	Intermediate Similarity	NPC114540
0.8	Intermediate Similarity	NPC84271
0.8	Intermediate Similarity	NPC206735
0.8	Intermediate Similarity	NPC262858
0.8	Intermediate Similarity	NPC2983
0.8	Intermediate Similarity	NPC473999
0.8	Intermediate Similarity	NPC472240
0.8	Intermediate Similarity	NPC30522
0.8	Intermediate Similarity	NPC474570
0.8	Intermediate Similarity	NPC309603
0.8	Intermediate Similarity	NPC251680
0.8	Intermediate Similarity	NPC477521
0.8	Intermediate Similarity	NPC471041
0.8	Intermediate Similarity	NPC77168
0.8	Intermediate Similarity	NPC102414
0.798	Intermediate Similarity	NPC110937
0.798	Intermediate Similarity	NPC291634
0.798	Intermediate Similarity	NPC156546
0.798	Intermediate Similarity	NPC253826
0.798	Intermediate Similarity	NPC10057
0.798	Intermediate Similarity	NPC475894
0.798	Intermediate Similarity	NPC57416
0.798	Intermediate Similarity	NPC126815
0.7979	Intermediate Similarity	NPC236618
0.7979	Intermediate Similarity	NPC46912
0.7979	Intermediate Similarity	NPC162107
0.7979	Intermediate Similarity	NPC33768
0.7959	Intermediate Similarity	NPC271195
0.7959	Intermediate Similarity	NPC83693
0.7959	Intermediate Similarity	NPC69548
0.7959	Intermediate Similarity	NPC259286
0.7959	Intermediate Similarity	NPC184848
0.7957	Intermediate Similarity	NPC264317
0.7957	Intermediate Similarity	NPC294438
0.7957	Intermediate Similarity	NPC471224
0.7944	Intermediate Similarity	NPC122056
0.7941	Intermediate Similarity	NPC297617
0.7941	Intermediate Similarity	NPC176883
0.7938	Intermediate Similarity	NPC470375
0.7938	Intermediate Similarity	NPC141497
0.7938	Intermediate Similarity	NPC470376
0.7938	Intermediate Similarity	NPC107674
0.7938	Intermediate Similarity	NPC49776
0.7938	Intermediate Similarity	NPC63118
0.7938	Intermediate Similarity	NPC472871
0.7938	Intermediate Similarity	NPC471902
0.7938	Intermediate Similarity	NPC287118
0.7938	Intermediate Similarity	NPC170220
0.7938	Intermediate Similarity	NPC12722
0.7938	Intermediate Similarity	NPC474436
0.7938	Intermediate Similarity	NPC473690
0.7938	Intermediate Similarity	NPC86368
0.7935	Intermediate Similarity	NPC470558
0.7935	Intermediate Similarity	NPC215893

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 NPC84383 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	1487
0.2-0.3	3992
0.3-0.4	2383
0.4-0.5	656
0.5-0.6	176
0.6-0.7	213
0.7-0.8	90
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
0.8021	Intermediate Similarity	NPD8035	Phase 2
0.8021	Intermediate Similarity	NPD8034	Phase 2
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.7957	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.79	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7708	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7521	Approved
0.7684	Intermediate Similarity	NPD6684	Approved
0.7684	Intermediate Similarity	NPD7334	Approved
0.7684	Intermediate Similarity	NPD5330	Approved
0.7684	Intermediate Similarity	NPD7146	Approved
0.7684	Intermediate Similarity	NPD6409	Approved
0.766	Intermediate Similarity	NPD4786	Approved
0.7653	Intermediate Similarity	NPD6079	Approved
0.7642	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6881	Approved
0.7629	Intermediate Similarity	NPD5328	Approved
0.7624	Intermediate Similarity	NPD7902	Approved
0.7619	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD5739	Approved
0.7619	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD7128	Approved
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7547	Intermediate Similarity	NPD5697	Approved
0.7526	Intermediate Similarity	NPD6903	Approved
0.7526	Intermediate Similarity	NPD6672	Approved
0.7526	Intermediate Similarity	NPD5737	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6001	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7475	Intermediate Similarity	NPD7515	Phase 2
0.7451	Intermediate Similarity	NPD6083	Phase 2
0.7451	Intermediate Similarity	NPD6084	Phase 2
0.7447	Intermediate Similarity	NPD3667	Approved
0.7431	Intermediate Similarity	NPD6617	Approved
0.7431	Intermediate Similarity	NPD6869	Approved
0.7431	Intermediate Similarity	NPD6649	Approved
0.7431	Intermediate Similarity	NPD6847	Approved
0.7431	Intermediate Similarity	NPD6650	Approved
0.7419	Intermediate Similarity	NPD7525	Registered
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6372	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD6373	Approved
0.7407	Intermediate Similarity	NPD6014	Approved
0.74	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5701	Approved
0.7364	Intermediate Similarity	NPD6882	Approved
0.7363	Intermediate Similarity	NPD6117	Approved
0.7333	Intermediate Similarity	NPD5211	Phase 2
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.729	Intermediate Similarity	NPD6008	Approved
0.7283	Intermediate Similarity	NPD6116	Phase 1
0.7273	Intermediate Similarity	NPD6673	Approved
0.7273	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD6051	Approved
0.7273	Intermediate Similarity	NPD6904	Approved
0.7273	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5695	Phase 3
0.7245	Intermediate Similarity	NPD3573	Approved
0.7212	Intermediate Similarity	NPD5696	Approved
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6697	Approved
0.7204	Intermediate Similarity	NPD6118	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7196	Intermediate Similarity	NPD5141	Approved
0.7184	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5221	Approved
0.7184	Intermediate Similarity	NPD5222	Approved
0.7172	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7129	Intermediate Similarity	NPD7637	Suspended
0.7115	Intermediate Similarity	NPD5173	Approved
0.7115	Intermediate Similarity	NPD4755	Approved
0.7113	Intermediate Similarity	NPD3668	Phase 3
0.7113	Intermediate Similarity	NPD3133	Approved
0.7113	Intermediate Similarity	NPD3665	Phase 1
0.7113	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD4223	Phase 3
0.7083	Intermediate Similarity	NPD4221	Approved
0.7083	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5223	Approved
0.7043	Intermediate Similarity	NPD6335	Approved
0.7041	Intermediate Similarity	NPD5329	Approved
0.7041	Intermediate Similarity	NPD1694	Approved
0.7034	Intermediate Similarity	NPD7604	Phase 2
0.703	Intermediate Similarity	NPD5207	Approved
0.7019	Intermediate Similarity	NPD4697	Phase 3
0.7018	Intermediate Similarity	NPD6868	Approved
0.701	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD4788	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD5225	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.6983	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD7100	Approved
0.6981	Remote Similarity	NPD4700	Approved
0.697	Remote Similarity	NPD4519	Discontinued
0.697	Remote Similarity	NPD4623	Approved
0.6961	Remote Similarity	NPD5284	Approved
0.6961	Remote Similarity	NPD5694	Approved
0.6961	Remote Similarity	NPD6050	Approved
0.6961	Remote Similarity	NPD5281	Approved
0.6957	Remote Similarity	NPD6317	Approved
0.6944	Remote Similarity	NPD5174	Approved
0.6944	Remote Similarity	NPD5175	Approved
0.6939	Remote Similarity	NPD4197	Approved
0.6931	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5777	Approved
0.6923	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7507	Approved
0.6897	Remote Similarity	NPD6314	Approved
0.6897	Remote Similarity	NPD6313	Approved
0.6887	Remote Similarity	NPD4225	Approved
0.6882	Remote Similarity	NPD3702	Approved
0.6882	Remote Similarity	NPD7339	Approved
0.6882	Remote Similarity	NPD6942	Approved
0.687	Remote Similarity	NPD6274	Approved
0.6863	Remote Similarity	NPD5692	Phase 3
0.681	Remote Similarity	NPD6009	Approved
0.6803	Remote Similarity	NPD7736	Approved
0.68	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4689	Approved
0.68	Remote Similarity	NPD4693	Phase 3
0.68	Remote Similarity	NPD5205	Approved
0.68	Remote Similarity	NPD5690	Phase 2
0.68	Remote Similarity	NPD5279	Phase 3
0.68	Remote Similarity	NPD4688	Approved
0.68	Remote Similarity	NPD4138	Approved
0.68	Remote Similarity	NPD4690	Approved
0.6796	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD4754	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6319	Approved
0.6778	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5360	Phase 3
0.6771	Remote Similarity	NPD7645	Phase 2
0.6762	Remote Similarity	NPD5210	Approved
0.6762	Remote Similarity	NPD4629	Approved
0.6748	Remote Similarity	NPD7319	Approved
0.6735	Remote Similarity	NPD4270	Approved
0.6735	Remote Similarity	NPD4269	Approved
0.6733	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5778	Approved
0.6731	Remote Similarity	NPD5779	Approved
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6909	Approved
0.6723	Remote Similarity	NPD6908	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.6723	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD8039	Approved
0.6701	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4821	Approved
0.6701	Remote Similarity	NPD4820	Approved
0.6701	Remote Similarity	NPD4819	Approved
0.6701	Remote Similarity	NPD4822	Approved
0.6699	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD4729	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6639	Remote Similarity	NPD8377	Approved
0.6639	Remote Similarity	NPD6336	Discontinued
0.6639	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD8294	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD5959	Approved
0.6634	Remote Similarity	NPD5280	Approved
0.6634	Remote Similarity	NPD4694	Approved
0.6634	Remote Similarity	NPD5786	Approved
0.6633	Remote Similarity	NPD6902	Approved
0.6633	Remote Similarity	NPD5369	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