NPASS Compound

Structure

NPC186339 OpenBabel07101718182D 39 46 0 0 1 0 0 0 0 0999 V2000 -2.0084 2.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3956 -0.4819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6471 2.9160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5481 2.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3238 0.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3351 1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 0.2364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3013 2.2242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1840 0.4955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0509 2.3734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7379 1.7403 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5047 0.3154 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3865 -0.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 1.5623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7186 0.7006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7699 1.2067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.2580 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6394 2.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5229 0.8747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7219 1.9188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3351 1.7319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6037 0.7493 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5380 3.2319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9526 -1.7550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1854 3.2201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5178 0.7739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2670 1.3143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1957 1.0382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9126 0.0265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2910 0.4252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 7 1 0 0 0 0 6 26 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 2 1 6 0 0 0 12 19 1 0 0 0 0 12 24 1 0 0 0 0 13 18 1 0 0 0 0 13 30 1 1 0 0 0 14 25 1 0 0 0 0 14 28 1 1 0 0 0 15 28 1 6 0 0 0 15 36 1 0 0 0 0 16 31 2 0 0 0 0 16 37 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 18 27 1 6 0 0 0 19 20 1 0 0 0 0 19 38 1 6 0 0 0 20 17 1 6 0 0 0 20 35 1 0 0 0 0 21 26 1 1 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 23 33 2 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 5 1 6 0 0 0 27 7 1 1 0 0 0 27 39 1 0 0 0 0 28 10 1 1 0 0 0 28 37 1 0 0 0 0 29 23 1 6 0 0 0 29 38 1 0 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.22
Volume:	516.408
LogP:	2.279
LogD:	1.466
LogS:	-4.506
# Rotatable Bonds:	0
TPSA:	134.66
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	7.546
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372
MDCK Permeability:	5.809473805129528e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.803
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	37.70540237426758%
Volume Distribution (VD):	1.125
Pgp-substrate:	43.138214111328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.705
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	15.6
Half-life (T1/2):	0.031

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.982
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.678
Carcinogencity:	0.535
Eye Corrosion:	0.016
Eye Irritation:	0.009
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC186339

Natural Product ID:	NPC186339
*Common Name:**	Lancifodilactone M
IUPAC Name:	n.a.
Synonyms:	Lancifodilactone M
Standard InCHIKey:	FWLVCPFAYYHJBG-MOFGTYHGSA-N
Standard InCHI:	InChI=1S/C29H34O10/c1-11-17-20-19(12(2)24(34)35-20)38-29-21(17)26(5,22(11)32)6-7-27(39-29)10-28-14(8-13(30)18(27)23(29)33)25(3,4)36-15(28)9-16(31)37-28/h12-15,18-21,30H,6-10H2,1-5H3/t12-,13-,14-,15+,18-,19+,20+,21-,26-,27-,28+,29-/m0/s1
SMILES:	O=C1C[C@@H]2[C@@]3(O1)C[C@]14CC[C@]5([C@H]6[C@](O1)(C(=O)[C@@H]4[C@H](C[C@H]3C(O2)(C)C)O)O[C@@H]1[C@H](C)C(=O)O[C@@H]1C6=C(C5=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499205
PubChem CID:	11519539
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787482]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	leaf	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[15901155]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499331]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643044]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19507	Schisandra lancifolia	Species	Schisandraceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200.0	ug.mL-1	PMID[540336]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	76.6	ug.mL-1	PMID[540336]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	2.61	n.a.	PMID[540336]

☑ 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 NPC186339 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	331
0.1-0.2	2208
0.2-0.3	7093
0.3-0.4	12726
0.4-0.5	11295
0.5-0.6	7012
0.6-0.7	1918
0.7-0.8	96
0.8-0.85	8
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9244	High Similarity	NPC11732
0.9024	High Similarity	NPC224623
0.9016	High Similarity	NPC469351
0.8992	High Similarity	NPC1538
0.8908	High Similarity	NPC192309
0.8852	High Similarity	NPC172823
0.8833	High Similarity	NPC42747
0.878	High Similarity	NPC13071
0.8739	High Similarity	NPC163693
0.8739	High Similarity	NPC147635
0.8455	Intermediate Similarity	NPC144625
0.8348	Intermediate Similarity	NPC469788
0.8348	Intermediate Similarity	NPC469787
0.8348	Intermediate Similarity	NPC290247
0.8205	Intermediate Similarity	NPC217041
0.8136	Intermediate Similarity	NPC182185
0.8103	Intermediate Similarity	NPC228311
0.8103	Intermediate Similarity	NPC41674
0.8103	Intermediate Similarity	NPC469441
0.8	Intermediate Similarity	NPC98870
0.7966	Intermediate Similarity	NPC329876
0.7931	Intermediate Similarity	NPC469350
0.7881	Intermediate Similarity	NPC176756
0.7833	Intermediate Similarity	NPC475463
0.7815	Intermediate Similarity	NPC278693
0.7815	Intermediate Similarity	NPC220773
0.7815	Intermediate Similarity	NPC167044
0.7805	Intermediate Similarity	NPC277583
0.7787	Intermediate Similarity	NPC209058
0.7759	Intermediate Similarity	NPC162024
0.7712	Intermediate Similarity	NPC472756
0.7712	Intermediate Similarity	NPC472748
0.7667	Intermediate Similarity	NPC475960
0.7647	Intermediate Similarity	NPC472749
0.7647	Intermediate Similarity	NPC472751
0.7647	Intermediate Similarity	NPC252234
0.7647	Intermediate Similarity	NPC168890
0.7627	Intermediate Similarity	NPC472747
0.7627	Intermediate Similarity	NPC472750
0.76	Intermediate Similarity	NPC471145
0.76	Intermediate Similarity	NPC475323
0.76	Intermediate Similarity	NPC471146
0.7586	Intermediate Similarity	NPC274695
0.7563	Intermediate Similarity	NPC203659
0.7561	Intermediate Similarity	NPC471570
0.7542	Intermediate Similarity	NPC472754
0.7541	Intermediate Similarity	NPC471884
0.7519	Intermediate Similarity	NPC471392
0.7519	Intermediate Similarity	NPC129992
0.7479	Intermediate Similarity	NPC475871
0.7479	Intermediate Similarity	NPC472755
0.7479	Intermediate Similarity	NPC475945
0.7479	Intermediate Similarity	NPC110989
0.7459	Intermediate Similarity	NPC475588
0.7459	Intermediate Similarity	NPC273433
0.7458	Intermediate Similarity	NPC472753
0.7438	Intermediate Similarity	NPC26617
0.7417	Intermediate Similarity	NPC474917
0.7402	Intermediate Similarity	NPC161060
0.7398	Intermediate Similarity	NPC477103
0.7395	Intermediate Similarity	NPC313569
0.7395	Intermediate Similarity	NPC474747
0.7395	Intermediate Similarity	NPC225353
0.7395	Intermediate Similarity	NPC86077
0.7388	Intermediate Similarity	NPC180902
0.7388	Intermediate Similarity	NPC475139
0.7385	Intermediate Similarity	NPC469352
0.7368	Intermediate Similarity	NPC476854
0.7368	Intermediate Similarity	NPC476851
0.7368	Intermediate Similarity	NPC472770
0.7364	Intermediate Similarity	NPC471999
0.7364	Intermediate Similarity	NPC470829
0.7364	Intermediate Similarity	NPC472000
0.7364	Intermediate Similarity	NPC473228
0.7355	Intermediate Similarity	NPC314244
0.7345	Intermediate Similarity	NPC32922
0.7339	Intermediate Similarity	NPC287311
0.7339	Intermediate Similarity	NPC474750
0.7333	Intermediate Similarity	NPC475873
0.7323	Intermediate Similarity	NPC475305
0.7323	Intermediate Similarity	NPC475238
0.7323	Intermediate Similarity	NPC36754
0.7323	Intermediate Similarity	NPC473656
0.7317	Intermediate Similarity	NPC477102
0.7313	Intermediate Similarity	NPC476852
0.7313	Intermediate Similarity	NPC476855
0.7311	Intermediate Similarity	NPC474742
0.7304	Intermediate Similarity	NPC471483
0.7302	Intermediate Similarity	NPC471382
0.7293	Intermediate Similarity	NPC188291
0.7288	Intermediate Similarity	NPC54843
0.7287	Intermediate Similarity	NPC329008
0.7287	Intermediate Similarity	NPC317635
0.7279	Intermediate Similarity	NPC471137
0.7279	Intermediate Similarity	NPC475154
0.7279	Intermediate Similarity	NPC471234
0.7279	Intermediate Similarity	NPC182266
0.7279	Intermediate Similarity	NPC223356
0.7279	Intermediate Similarity	NPC100017
0.7279	Intermediate Similarity	NPC471136
0.7279	Intermediate Similarity	NPC473548
0.7279	Intermediate Similarity	NPC475500
0.7273	Intermediate Similarity	NPC100487
0.7273	Intermediate Similarity	NPC474741
0.7273	Intermediate Similarity	NPC217901
0.7266	Intermediate Similarity	NPC475401
0.7266	Intermediate Similarity	NPC13710
0.7266	Intermediate Similarity	NPC475309
0.7265	Intermediate Similarity	NPC476009
0.7259	Intermediate Similarity	NPC100390
0.7259	Intermediate Similarity	NPC472769
0.7259	Intermediate Similarity	NPC254614
0.7258	Intermediate Similarity	NPC48305
0.7258	Intermediate Similarity	NPC257240
0.7258	Intermediate Similarity	NPC474923
0.725	Intermediate Similarity	NPC320019
0.725	Intermediate Similarity	NPC324017
0.7241	Intermediate Similarity	NPC471496
0.7239	Intermediate Similarity	NPC162495
0.7231	Intermediate Similarity	NPC472001
0.7218	Intermediate Similarity	NPC298841
0.7218	Intermediate Similarity	NPC475273
0.7218	Intermediate Similarity	NPC168849
0.7213	Intermediate Similarity	NPC243998
0.7213	Intermediate Similarity	NPC475217
0.7213	Intermediate Similarity	NPC469401
0.7213	Intermediate Similarity	NPC223450
0.7209	Intermediate Similarity	NPC477092
0.7209	Intermediate Similarity	NPC178548
0.7209	Intermediate Similarity	NPC258592
0.7206	Intermediate Similarity	NPC168879
0.7197	Intermediate Similarity	NPC470922
0.719	Intermediate Similarity	NPC473148
0.719	Intermediate Similarity	NPC4620
0.7185	Intermediate Similarity	NPC251564
0.7185	Intermediate Similarity	NPC475314
0.7185	Intermediate Similarity	NPC473838
0.7185	Intermediate Similarity	NPC477189
0.7185	Intermediate Similarity	NPC475606
0.7185	Intermediate Similarity	NPC475389
0.7179	Intermediate Similarity	NPC475900
0.7179	Intermediate Similarity	NPC473334
0.7174	Intermediate Similarity	NPC243014
0.7174	Intermediate Similarity	NPC68282
0.7167	Intermediate Similarity	NPC133907
0.7167	Intermediate Similarity	NPC476270
0.7167	Intermediate Similarity	NPC46998
0.7167	Intermediate Similarity	NPC128733
0.7167	Intermediate Similarity	NPC185141
0.7167	Intermediate Similarity	NPC171759
0.7167	Intermediate Similarity	NPC15993
0.7167	Intermediate Similarity	NPC110443
0.7165	Intermediate Similarity	NPC471380
0.7165	Intermediate Similarity	NPC475537
0.7165	Intermediate Similarity	NPC308858
0.7164	Intermediate Similarity	NPC476859
0.7155	Intermediate Similarity	NPC135776
0.7154	Intermediate Similarity	NPC474421
0.7154	Intermediate Similarity	NPC204884
0.7154	Intermediate Similarity	NPC324327
0.7154	Intermediate Similarity	NPC72813
0.7154	Intermediate Similarity	NPC194620
0.7154	Intermediate Similarity	NPC326994
0.7153	Intermediate Similarity	NPC15215
0.7153	Intermediate Similarity	NPC242486
0.7143	Intermediate Similarity	NPC472015
0.7143	Intermediate Similarity	NPC222307
0.7143	Intermediate Similarity	NPC141191
0.7132	Intermediate Similarity	NPC473485
0.7132	Intermediate Similarity	NPC102316
0.7132	Intermediate Similarity	NPC474508
0.7132	Intermediate Similarity	NPC475372
0.7131	Intermediate Similarity	NPC114365
0.7131	Intermediate Similarity	NPC18433
0.7131	Intermediate Similarity	NPC132304
0.7131	Intermediate Similarity	NPC475676
0.7131	Intermediate Similarity	NPC88890
0.7131	Intermediate Similarity	NPC169089
0.7131	Intermediate Similarity	NPC123070
0.7131	Intermediate Similarity	NPC154962
0.7131	Intermediate Similarity	NPC18044
0.7131	Intermediate Similarity	NPC177518
0.7131	Intermediate Similarity	NPC220964
0.7121	Intermediate Similarity	NPC472399
0.7121	Intermediate Similarity	NPC67251
0.7121	Intermediate Similarity	NPC91693
0.7121	Intermediate Similarity	NPC472768
0.7121	Intermediate Similarity	NPC265557
0.7121	Intermediate Similarity	NPC18945
0.7121	Intermediate Similarity	NPC105926
0.7111	Intermediate Similarity	NPC264192
0.7109	Intermediate Similarity	NPC54739
0.7107	Intermediate Similarity	NPC105725
0.7107	Intermediate Similarity	NPC149371
0.7099	Intermediate Similarity	NPC470779
0.7099	Intermediate Similarity	NPC278163
0.7099	Intermediate Similarity	NPC258815
0.7099	Intermediate Similarity	NPC241310
0.7099	Intermediate Similarity	NPC258789
0.7099	Intermediate Similarity	NPC194310

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 NPC186339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	2714
0.2-0.3	3901
0.3-0.4	1467
0.4-0.5	493
0.5-0.6	194
0.6-0.7	32
0.7-0.8	1
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
0.7438	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6371	Approved
0.7131	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7078	Approved
0.6815	Remote Similarity	NPD7492	Approved
0.6807	Remote Similarity	NPD5282	Discontinued
0.6767	Remote Similarity	NPD6059	Approved
0.6767	Remote Similarity	NPD6054	Approved
0.6765	Remote Similarity	NPD6616	Approved
0.6739	Remote Similarity	NPD7319	Approved
0.6716	Remote Similarity	NPD8268	Approved
0.6716	Remote Similarity	NPD8266	Approved
0.6716	Remote Similarity	NPD8267	Approved
0.6716	Remote Similarity	NPD8269	Approved
0.6715	Remote Similarity	NPD8293	Discontinued
0.6693	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6642	Remote Similarity	NPD7507	Approved
0.6593	Remote Similarity	NPD6016	Approved
0.6593	Remote Similarity	NPD6015	Approved
0.6555	Remote Similarity	NPD6698	Approved
0.6555	Remote Similarity	NPD46	Approved
0.6544	Remote Similarity	NPD5988	Approved
0.6541	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8328	Phase 3
0.6489	Remote Similarity	NPD6053	Discontinued
0.6479	Remote Similarity	NPD6845	Suspended
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8080	Discontinued
0.6397	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6333	Remote Similarity	NPD1695	Approved
0.632	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD6033	Approved
0.6308	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6009	Approved
0.6294	Remote Similarity	NPD7260	Phase 2
0.626	Remote Similarity	NPD6373	Approved
0.626	Remote Similarity	NPD6372	Approved
0.6259	Remote Similarity	NPD7642	Approved
0.6241	Remote Similarity	NPD8297	Approved
0.6241	Remote Similarity	NPD8074	Phase 3
0.6232	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7983	Approved
0.6183	Remote Similarity	NPD7320	Approved
0.6176	Remote Similarity	NPD7115	Discovery
0.6165	Remote Similarity	NPD6650	Approved
0.6165	Remote Similarity	NPD6649	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6148	Remote Similarity	NPD5785	Approved
0.6131	Remote Similarity	NPD7327	Approved
0.6131	Remote Similarity	NPD7328	Approved
0.6115	Remote Similarity	NPD8033	Approved
0.6115	Remote Similarity	NPD8444	Approved
0.6107	Remote Similarity	NPD6412	Phase 2
0.609	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7516	Approved
0.6063	Remote Similarity	NPD5696	Approved
0.6063	Remote Similarity	NPD4225	Approved
0.6061	Remote Similarity	NPD6899	Approved
0.6061	Remote Similarity	NPD6881	Approved
0.6043	Remote Similarity	NPD8377	Approved
0.6043	Remote Similarity	NPD8294	Approved
0.6032	Remote Similarity	NPD7839	Suspended
0.6017	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8296	Approved
0.6	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD8335	Approved
0.6	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD8380	Approved
0.5985	Remote Similarity	NPD5701	Approved
0.5985	Remote Similarity	NPD5697	Approved
0.5984	Remote Similarity	NPD6083	Phase 2
0.5984	Remote Similarity	NPD6084	Phase 2
0.597	Remote Similarity	NPD6883	Approved
0.597	Remote Similarity	NPD7290	Approved
0.597	Remote Similarity	NPD7102	Approved
0.5969	Remote Similarity	NPD1700	Approved
0.5956	Remote Similarity	NPD8133	Approved
0.5956	Remote Similarity	NPD4632	Approved
0.5944	Remote Similarity	NPD8451	Approved
0.5942	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6847	Approved
0.5926	Remote Similarity	NPD8130	Phase 1
0.5926	Remote Similarity	NPD6869	Approved
0.5926	Remote Similarity	NPD6617	Approved
0.592	Remote Similarity	NPD5779	Approved
0.592	Remote Similarity	NPD5778	Approved
0.5915	Remote Similarity	NPD7604	Phase 2
0.5915	Remote Similarity	NPD7830	Approved
0.5915	Remote Similarity	NPD7829	Approved
0.5909	Remote Similarity	NPD6008	Approved
0.5903	Remote Similarity	NPD8448	Approved
0.5896	Remote Similarity	NPD6013	Approved
0.5896	Remote Similarity	NPD6012	Approved
0.5896	Remote Similarity	NPD6014	Approved
0.5887	Remote Similarity	NPD6921	Approved
0.5887	Remote Similarity	NPD5983	Phase 2
0.5887	Remote Similarity	NPD7838	Discovery
0.5887	Remote Similarity	NPD7503	Approved
0.5868	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD8336	Approved
0.5862	Remote Similarity	NPD8337	Approved
0.584	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD6336	Discontinued
0.5827	Remote Similarity	NPD5695	Phase 3
0.5821	Remote Similarity	NPD6011	Approved
0.582	Remote Similarity	NPD5786	Approved
0.5814	Remote Similarity	NPD7638	Approved
0.5809	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD7641	Discontinued
0.5782	Remote Similarity	NPD8390	Approved
0.5782	Remote Similarity	NPD8391	Approved
0.5782	Remote Similarity	NPD8392	Approved
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5764	Remote Similarity	NPD8340	Approved
0.5764	Remote Similarity	NPD8342	Approved
0.5764	Remote Similarity	NPD8341	Approved
0.5764	Remote Similarity	NPD8299	Approved
0.5738	Remote Similarity	NPD5363	Approved
0.5735	Remote Similarity	NPD4634	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5705	Remote Similarity	NPD8338	Approved
0.5702	Remote Similarity	NPD5362	Discontinued
0.5698	Remote Similarity	NPD7799	Discontinued
0.5695	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7632	Discontinued
0.568	Remote Similarity	NPD6101	Approved
0.568	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6399	Phase 3
0.5667	Remote Similarity	NPD5369	Approved
0.5645	Remote Similarity	NPD4251	Approved
0.5645	Remote Similarity	NPD4250	Approved
0.5643	Remote Similarity	NPD6274	Approved
0.5634	Remote Similarity	NPD7100	Approved
0.5634	Remote Similarity	NPD7101	Approved
0.5629	Remote Similarity	NPD8415	Approved
0.562	Remote Similarity	NPD4270	Approved
0.562	Remote Similarity	NPD6435	Approved
0.562	Remote Similarity	NPD4269	Approved
0.5616	Remote Similarity	NPD8273	Phase 1
0.5615	Remote Similarity	NPD4755	Approved
0.561	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.561	Remote Similarity	NPD1694	Approved
0.5606	Remote Similarity	NPD5344	Discontinued
0.56	Remote Similarity	NPD5737	Approved
0.56	Remote Similarity	NPD6672	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