NPASS Compound

Structure

NPC211845 OpenBabel07101719522D 37 42 0 0 1 0 0 0 0 0999 V2000 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5031 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 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 -6.0390 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8477 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1730 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3070 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9051 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9051 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3070 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5031 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3070 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4410 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7711 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1730 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7711 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9021 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1730 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4899 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4410 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3692 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6371 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0390 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6371 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.6910 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 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 10 17 1 0 0 0 0 10 22 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 13 27 1 0 0 0 0 14 21 1 0 0 0 0 14 28 1 0 0 0 0 15 1 1 6 0 0 0 15 26 1 0 0 0 0 16 31 2 0 0 0 0 16 35 1 0 0 0 0 17 27 1 1 0 0 0 18 9 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 28 1 1 0 0 0 20 22 1 0 0 0 0 20 32 1 6 0 0 0 21 24 1 0 0 0 0 21 33 1 1 0 0 0 22 35 1 6 0 0 0 23 11 1 1 0 0 0 23 25 1 0 0 0 0 23 36 1 0 0 0 0 24 27 1 1 0 0 0 25 28 1 1 0 0 0 25 29 1 0 0 0 0 26 37 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 29 34 1 0 0 0 0 30 12 1 6 0 0 0 30 36 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.34
Volume:	534.992
LogP:	4.536
LogD:	3.757
LogS:	-4.458
# Rotatable Bonds:	2
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	6.0
Fsp3:	0.967
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:	-5.169
MDCK Permeability:	6.347236194415018e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.306

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.312
Plasma Protein Binding (PPB):	64.71671295166016%
Volume Distribution (VD):	0.841
Pgp-substrate:	24.119335174560547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.593

ADMET: Excretion

Clearance (CL):	9.924
Half-life (T1/2):	0.417

ADMET: Toxicity

hERG Blockers:	0.726
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.339
Rat Oral Acute Toxicity:	0.696
Maximum Recommended Daily Dose:	0.583
Skin Sensitization:	0.932
Carcinogencity:	0.734
Eye Corrosion:	0.019
Eye Irritation:	0.024
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC211845

Natural Product ID:	NPC211845
*Common Name:**	CLRGSPLGNCTOOL-YKVVPRMGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CLRGSPLGNCTOOL-YKVVPRMGSA-N
Standard InCHI:	InChI=1S/C30H48O7/c1-15-12-30(37-26(15,3)4)29(7,34)25-23(36-30)11-19-18-9-8-17-10-22(35-16(2)31)20(32)13-27(17,5)24(18)21(33)14-28(19,25)6/h15,17-25,32-34H,8-14H2,1-7H3/t15-,17-,18-,19-,20+,21-,22-,23-,24+,25-,27-,28-,29+,30+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@@](C)([C@H]3[C@H](C[C@H]4[C@@H]5CC[C@H]6C[C@@H]([C@@H](C[C@]6(C)[C@H]5[C@H](C[C@]34C)O)O)OC(=O)C)O2)O)OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507260
PubChem CID:	11443805
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001702] Furospirostanes 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
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141096]
NPO19653	Isis hippuris	Species	Isididae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974612]
NPO19653	Isis hippuris	Species	Isididae	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
IC50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.72	ug.mL-1	PMID[511081]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.07	ug.mL-1	PMID[511081]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	0.21	ug.mL-1	PMID[511081]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.46	ug.mL-1	PMID[511081]
NPT22886	SINGLE PROTEIN	Eukaryotic initiation factor 4A-I	Mus musculus	IC50	=	1700.0	nM	PMID[511082]

☑ 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 NPC211845 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	461
0.1-0.2	3971
0.2-0.3	12362
0.3-0.4	11451
0.4-0.5	5685
0.5-0.6	4961
0.6-0.7	2827
0.7-0.8	853
0.8-0.85	98
0.85-0.9	19
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC256104
1.0	High Similarity	NPC182740
1.0	High Similarity	NPC122083
0.9535	High Similarity	NPC128475
0.9419	High Similarity	NPC210658
0.9419	High Similarity	NPC161928
0.9333	High Similarity	NPC21897
0.9239	High Similarity	NPC292775
0.9022	High Similarity	NPC156377
0.8966	High Similarity	NPC266651
0.8958	High Similarity	NPC100078
0.8866	High Similarity	NPC166079
0.8864	High Similarity	NPC155531
0.8864	High Similarity	NPC215968
0.8837	High Similarity	NPC470611
0.8791	High Similarity	NPC473066
0.8778	High Similarity	NPC20822
0.875	High Similarity	NPC213528
0.875	High Similarity	NPC273290
0.875	High Similarity	NPC244969
0.875	High Similarity	NPC232044
0.8737	High Similarity	NPC470030
0.8736	High Similarity	NPC477285
0.8736	High Similarity	NPC111582
0.8696	High Similarity	NPC35164
0.8673	High Similarity	NPC306776
0.8652	High Similarity	NPC477283
0.8646	High Similarity	NPC108227
0.8646	High Similarity	NPC476512
0.8646	High Similarity	NPC472081
0.8646	High Similarity	NPC475574
0.8636	High Similarity	NPC227260
0.8636	High Similarity	NPC18953
0.8621	High Similarity	NPC202688
0.8621	High Similarity	NPC60018
0.8621	High Similarity	NPC154043
0.8621	High Similarity	NPC286719
0.8621	High Similarity	NPC477286
0.8617	High Similarity	NPC203434
0.8617	High Similarity	NPC238796
0.8617	High Similarity	NPC145553
0.8617	High Similarity	NPC237071
0.8602	High Similarity	NPC477224
0.8602	High Similarity	NPC3538
0.8602	High Similarity	NPC113500
0.8587	High Similarity	NPC149966
0.8587	High Similarity	NPC5632
0.8571	High Similarity	NPC228059
0.8557	High Similarity	NPC310138
0.8557	High Similarity	NPC114700
0.8557	High Similarity	NPC470029
0.8557	High Similarity	NPC134967
0.8556	High Similarity	NPC213658
0.8556	High Similarity	NPC5943
0.8556	High Similarity	NPC62202
0.8556	High Similarity	NPC45833
0.8556	High Similarity	NPC110365
0.8523	High Similarity	NPC470070
0.8511	High Similarity	NPC57964
0.8511	High Similarity	NPC94582
0.8506	High Similarity	NPC190940
0.8495	Intermediate Similarity	NPC167644
0.8495	Intermediate Similarity	NPC311246
0.8488	Intermediate Similarity	NPC476176
0.8478	Intermediate Similarity	NPC473542
0.8469	Intermediate Similarity	NPC139181
0.8469	Intermediate Similarity	NPC97260
0.8469	Intermediate Similarity	NPC476837
0.8462	Intermediate Similarity	NPC470872
0.8454	Intermediate Similarity	NPC477225
0.8444	Intermediate Similarity	NPC131365
0.8444	Intermediate Similarity	NPC471410
0.8444	Intermediate Similarity	NPC471240
0.8444	Intermediate Similarity	NPC471411
0.8421	Intermediate Similarity	NPC296936
0.8421	Intermediate Similarity	NPC116683
0.8409	Intermediate Similarity	NPC296734
0.8409	Intermediate Similarity	NPC475388
0.8404	Intermediate Similarity	NPC191915
0.8404	Intermediate Similarity	NPC45959
0.8404	Intermediate Similarity	NPC30687
0.8404	Intermediate Similarity	NPC175
0.8404	Intermediate Similarity	NPC151214
0.8404	Intermediate Similarity	NPC252253
0.8387	Intermediate Similarity	NPC59006
0.8387	Intermediate Similarity	NPC293609
0.8372	Intermediate Similarity	NPC471045
0.837	Intermediate Similarity	NPC82955
0.837	Intermediate Similarity	NPC473472
0.8333	Intermediate Similarity	NPC290612
0.8333	Intermediate Similarity	NPC477222
0.8333	Intermediate Similarity	NPC477223
0.8333	Intermediate Similarity	NPC470591
0.8316	Intermediate Similarity	NPC473067
0.8316	Intermediate Similarity	NPC473065
0.8316	Intermediate Similarity	NPC473064
0.8298	Intermediate Similarity	NPC88962
0.8298	Intermediate Similarity	NPC475307
0.8298	Intermediate Similarity	NPC472232
0.8298	Intermediate Similarity	NPC144790
0.8298	Intermediate Similarity	NPC149400
0.8298	Intermediate Similarity	NPC472231
0.8298	Intermediate Similarity	NPC277774
0.828	Intermediate Similarity	NPC279329
0.828	Intermediate Similarity	NPC223143
0.8276	Intermediate Similarity	NPC477287
0.8276	Intermediate Similarity	NPC81074
0.8276	Intermediate Similarity	NPC477282
0.8265	Intermediate Similarity	NPC476839
0.8265	Intermediate Similarity	NPC476838
0.8261	Intermediate Similarity	NPC56777
0.8261	Intermediate Similarity	NPC281004
0.8261	Intermediate Similarity	NPC201607
0.8256	Intermediate Similarity	NPC171658
0.8256	Intermediate Similarity	NPC11907
0.8256	Intermediate Similarity	NPC474574
0.8256	Intermediate Similarity	NPC64081
0.8256	Intermediate Similarity	NPC133596
0.8247	Intermediate Similarity	NPC473638
0.8242	Intermediate Similarity	NPC114378
0.8242	Intermediate Similarity	NPC103782
0.8235	Intermediate Similarity	NPC473570
0.8229	Intermediate Similarity	NPC121453
0.8229	Intermediate Similarity	NPC252056
0.8229	Intermediate Similarity	NPC139271
0.8229	Intermediate Similarity	NPC142264
0.8229	Intermediate Similarity	NPC476728
0.8229	Intermediate Similarity	NPC476510
0.8229	Intermediate Similarity	NPC475785
0.8229	Intermediate Similarity	NPC304011
0.8211	Intermediate Similarity	NPC24960
0.8211	Intermediate Similarity	NPC222731
0.8211	Intermediate Similarity	NPC291547
0.8211	Intermediate Similarity	NPC179859
0.8211	Intermediate Similarity	NPC174024
0.8211	Intermediate Similarity	NPC473774
0.8211	Intermediate Similarity	NPC294686
0.8211	Intermediate Similarity	NPC312678
0.8211	Intermediate Similarity	NPC131693
0.8211	Intermediate Similarity	NPC475436
0.8211	Intermediate Similarity	NPC473851
0.8211	Intermediate Similarity	NPC253268
0.8202	Intermediate Similarity	NPC470155
0.8202	Intermediate Similarity	NPC477447
0.8202	Intermediate Similarity	NPC477446
0.8202	Intermediate Similarity	NPC477284
0.8191	Intermediate Similarity	NPC229801
0.8191	Intermediate Similarity	NPC307167
0.8191	Intermediate Similarity	NPC210759
0.8191	Intermediate Similarity	NPC36372
0.819	Intermediate Similarity	NPC79193
0.8182	Intermediate Similarity	NPC474714
0.8182	Intermediate Similarity	NPC471216
0.8182	Intermediate Similarity	NPC248944
0.8182	Intermediate Similarity	NPC7479
0.8182	Intermediate Similarity	NPC472943
0.8182	Intermediate Similarity	NPC472951
0.8182	Intermediate Similarity	NPC471217
0.8182	Intermediate Similarity	NPC257296
0.8172	Intermediate Similarity	NPC102725
0.8152	Intermediate Similarity	NPC472396
0.8152	Intermediate Similarity	NPC140446
0.8152	Intermediate Similarity	NPC43912
0.8144	Intermediate Similarity	NPC471241
0.8144	Intermediate Similarity	NPC233649
0.8144	Intermediate Similarity	NPC470028
0.8144	Intermediate Similarity	NPC210157
0.814	Intermediate Similarity	NPC163597
0.8132	Intermediate Similarity	NPC235402
0.8125	Intermediate Similarity	NPC92196
0.8125	Intermediate Similarity	NPC474399
0.8125	Intermediate Similarity	NPC215570
0.8111	Intermediate Similarity	NPC69953
0.8111	Intermediate Similarity	NPC474253
0.8111	Intermediate Similarity	NPC474284
0.8111	Intermediate Similarity	NPC213737
0.8111	Intermediate Similarity	NPC475820
0.8111	Intermediate Similarity	NPC474346
0.8111	Intermediate Similarity	NPC29342
0.8111	Intermediate Similarity	NPC2572
0.8105	Intermediate Similarity	NPC325828
0.8105	Intermediate Similarity	NPC250393
0.8105	Intermediate Similarity	NPC297348
0.8105	Intermediate Similarity	NPC477547
0.8105	Intermediate Similarity	NPC141769
0.8105	Intermediate Similarity	NPC177834
0.8105	Intermediate Similarity	NPC249204
0.8105	Intermediate Similarity	NPC234352
0.8105	Intermediate Similarity	NPC477451
0.8105	Intermediate Similarity	NPC476669
0.8105	Intermediate Similarity	NPC48339
0.809	Intermediate Similarity	NPC71541
0.809	Intermediate Similarity	NPC73515
0.809	Intermediate Similarity	NPC470156
0.809	Intermediate Similarity	NPC470154
0.8085	Intermediate Similarity	NPC65550
0.8061	Intermediate Similarity	NPC473518
0.8046	Intermediate Similarity	NPC128951
0.8046	Intermediate Similarity	NPC105208
0.8046	Intermediate Similarity	NPC192046

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 NPC211845 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	463
0.1-0.2	4048
0.2-0.3	3279
0.3-0.4	725
0.4-0.5	319
0.5-0.6	228
0.6-0.7	75
0.7-0.8	13
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
0.8182	Intermediate Similarity	NPD6928	Phase 2
0.8105	Intermediate Similarity	NPD8171	Discontinued
0.767	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7516	Approved
0.7363	Intermediate Similarity	NPD6118	Approved
0.7363	Intermediate Similarity	NPD6697	Approved
0.7363	Intermediate Similarity	NPD6114	Approved
0.7363	Intermediate Similarity	NPD6115	Approved
0.7321	Intermediate Similarity	NPD7328	Approved
0.7321	Intermediate Similarity	NPD7327	Approved
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7212	Intermediate Similarity	NPD1700	Approved
0.7193	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD8294	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.713	Intermediate Similarity	NPD8380	Approved
0.713	Intermediate Similarity	NPD8296	Approved
0.713	Intermediate Similarity	NPD8033	Approved
0.713	Intermediate Similarity	NPD8335	Approved
0.713	Intermediate Similarity	NPD8379	Approved
0.713	Intermediate Similarity	NPD8378	Approved
0.7059	Intermediate Similarity	NPD7991	Discontinued
0.6966	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7507	Approved
0.6833	Remote Similarity	NPD7078	Approved
0.6807	Remote Similarity	NPD7492	Approved
0.6778	Remote Similarity	NPD4787	Phase 1
0.6777	Remote Similarity	NPD7736	Approved
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.6721	Remote Similarity	NPD7319	Approved
0.6696	Remote Similarity	NPD6940	Discontinued
0.6695	Remote Similarity	NPD7503	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD3702	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6633	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3669	Approved
0.6607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6412	Phase 2
0.6559	Remote Similarity	NPD1810	Approved
0.6559	Remote Similarity	NPD1811	Approved
0.6555	Remote Similarity	NPD6015	Approved
0.6555	Remote Similarity	NPD6016	Approved
0.6545	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5777	Approved
0.65	Remote Similarity	NPD5988	Approved
0.6496	Remote Similarity	NPD6009	Approved
0.6489	Remote Similarity	NPD3703	Phase 2
0.6481	Remote Similarity	NPD7640	Approved
0.6481	Remote Similarity	NPD7639	Approved
0.6477	Remote Similarity	NPD371	Approved
0.6442	Remote Similarity	NPD8035	Phase 2
0.6442	Remote Similarity	NPD8034	Phase 2
0.6435	Remote Similarity	NPD6882	Approved
0.6413	Remote Similarity	NPD4245	Approved
0.6413	Remote Similarity	NPD4244	Approved
0.6379	Remote Similarity	NPD4632	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7632	Discontinued
0.6339	Remote Similarity	NPD6675	Approved
0.6339	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD7128	Approved
0.6339	Remote Similarity	NPD6402	Approved
0.6337	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6319	Approved
0.6327	Remote Similarity	NPD7525	Registered
0.6316	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3698	Phase 2
0.6304	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8297	Approved
0.624	Remote Similarity	NPD6033	Approved
0.6237	Remote Similarity	NPD2686	Approved
0.6237	Remote Similarity	NPD2687	Approved
0.6237	Remote Similarity	NPD2254	Approved
0.6228	Remote Similarity	NPD6899	Approved
0.6228	Remote Similarity	NPD6881	Approved
0.6218	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5360	Phase 3
0.6195	Remote Similarity	NPD6008	Approved
0.6179	Remote Similarity	NPD6067	Discontinued
0.6174	Remote Similarity	NPD6373	Approved
0.6174	Remote Similarity	NPD6372	Approved
0.617	Remote Similarity	NPD6081	Approved
0.614	Remote Similarity	NPD5697	Approved
0.614	Remote Similarity	NPD5701	Approved
0.6121	Remote Similarity	NPD6883	Approved
0.6121	Remote Similarity	NPD7102	Approved
0.6121	Remote Similarity	NPD7290	Approved
0.61	Remote Similarity	NPD1779	Approved
0.61	Remote Similarity	NPD1780	Approved
0.6087	Remote Similarity	NPD6686	Approved
0.6087	Remote Similarity	NPD8174	Phase 2
0.6068	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD6649	Approved
0.6068	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6617	Approved
0.6068	Remote Similarity	NPD6869	Approved
0.6064	Remote Similarity	NPD4789	Approved
0.6058	Remote Similarity	NPD7524	Approved
0.6058	Remote Similarity	NPD7625	Phase 1
0.6048	Remote Similarity	NPD7604	Phase 2
0.6036	Remote Similarity	NPD8418	Phase 2
0.6034	Remote Similarity	NPD6012	Approved
0.6034	Remote Similarity	NPD6013	Approved
0.6034	Remote Similarity	NPD6014	Approved
0.6016	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.5983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4224	Phase 2
0.5952	Remote Similarity	NPD6336	Discontinued
0.5948	Remote Similarity	NPD6011	Approved
0.5932	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6399	Phase 3
0.592	Remote Similarity	NPD8328	Phase 3
0.587	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4755	Approved
0.5847	Remote Similarity	NPD4634	Approved
0.5841	Remote Similarity	NPD4159	Approved
0.5833	Remote Similarity	NPD4758	Discontinued
0.5825	Remote Similarity	NPD4788	Approved
0.582	Remote Similarity	NPD7115	Discovery
0.5818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4225	Approved
0.58	Remote Similarity	NPD5364	Discontinued
0.58	Remote Similarity	NPD3671	Phase 1
0.58	Remote Similarity	NPD4802	Phase 2
0.58	Remote Similarity	NPD4238	Approved
0.5794	Remote Similarity	NPD6051	Approved
0.578	Remote Similarity	NPD4202	Approved
0.5769	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5956	Approved
0.576	Remote Similarity	NPD6921	Approved
0.5752	Remote Similarity	NPD4700	Approved
0.5752	Remote Similarity	NPD5286	Approved
0.5752	Remote Similarity	NPD4696	Approved
0.5752	Remote Similarity	NPD5285	Approved
0.5741	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6700	Approved
0.5738	Remote Similarity	NPD6274	Approved
0.5726	Remote Similarity	NPD7101	Approved
0.5726	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7100	Approved
0.5726	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5344	Discontinued
0.5688	Remote Similarity	NPD6702	Approved
0.5688	Remote Similarity	NPD6703	Approved
0.5686	Remote Similarity	NPD4748	Discontinued
0.5682	Remote Similarity	NPD2267	Suspended
0.5682	Remote Similarity	NPD8449	Approved
0.5676	Remote Similarity	NPD5695	Phase 3
0.5673	Remote Similarity	NPD6695	Phase 3
0.5664	Remote Similarity	NPD5696	Approved
0.566	Remote Similarity	NPD8308	Discontinued
0.5652	Remote Similarity	NPD5225	Approved
0.5652	Remote Similarity	NPD4633	Approved
0.5652	Remote Similarity	NPD5224	Approved
0.5652	Remote Similarity	NPD5211	Phase 2
0.5652	Remote Similarity	NPD5226	Approved
0.5645	Remote Similarity	NPD6335	Approved
0.5639	Remote Similarity	NPD8450	Suspended
0.5635	Remote Similarity	NPD6908	Approved
0.5635	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6909	Approved
0.562	Remote Similarity	NPD6053	Discontinued
0.561	Remote Similarity	NPD7754	Approved
0.561	Remote Similarity	NPD7755	Approved
0.5607	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5174	Approved
0.5603	Remote Similarity	NPD5175	Approved
0.56	Remote Similarity	NPD3701	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