NPASS Compound

Structure

NPC472225 OpenBabel07101718252D 35 40 0 0 1 0 0 0 0 0999 V2000 2.4769 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4525 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7475 4.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7231 4.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3904 1.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2525 2.4698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2525 -0.2883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7006 3.0420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5455 3.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0802 2.0664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2353 1.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9279 1.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3544 1.0908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9279 -0.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9279 -1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7006 0.1152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5013 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5013 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7006 2.0664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5455 0.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3904 3.0420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0802 3.0420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5455 1.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9279 -2.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2353 3.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3904 2.0664 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8557 1.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8557 0.6030 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9279 0.3015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3904 0.1152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9251 3.5298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2293 -3.1806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 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 18 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 0 0 0 17 24 1 0 0 0 0 18 30 1 1 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 31 2 0 0 0 0 21 25 1 0 0 0 0 21 26 1 6 0 0 0 22 25 1 0 0 0 0 22 32 2 0 0 0 0 23 26 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 1 0 0 0 29 14 1 6 0 0 0 29 34 1 0 0 0 0 29 35 1 0 0 0 0 30 13 1 1 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	505.985
LogP:	5.224
LogD:	4.34
LogS:	-5.389
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	5.979
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:	-5.001
MDCK Permeability:	2.623611544549931e-05
Pgp-inhibitor:	0.404
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.44
Plasma Protein Binding (PPB):	92.58805847167969%
Volume Distribution (VD):	1.412
Pgp-substrate:	3.6875438690185547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.324
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.384
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	12.15
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.128
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.763
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.379
Carcinogencity:	0.101
Eye Corrosion:	0.016
Eye Irritation:	0.131
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC472225

Natural Product ID:	NPC472225
*Common Name:**	CSSUMQOYGVWJIF-XPNPTXLSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CSSUMQOYGVWJIF-XPNPTXLSSA-N
Standard InCHI:	InChI=1S/C30H42O5/c1-17-14-29(34-24(17)33)15-18(2)30(35-29)13-12-27(6)19-8-9-21-25(3,4)22(32)10-11-26(21,5)23(19)20(31)16-28(27,30)7/h17-18,21H,8-16H2,1-7H3/t17-,18-,21+,26+,27+,28+,29-,30-/m1/s1
SMILES:	C[C@@H]1C[C@]2(OC1=O)C[C@H]([C@]1(O2)CC[C@@]2([C@]1(C)CC(=O)C1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353333
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	31200.0	nM	PMID[449667]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[449667]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[449667]
NPT27	Others	Unspecified		IC50	=	26800.0	nM	PMID[449667]

☑ 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 NPC472225 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	275
0.1-0.2	2056
0.2-0.3	9677
0.3-0.4	14150
0.4-0.5	6711
0.5-0.6	7630
0.6-0.7	2016
0.7-0.8	174
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472226
0.9222	High Similarity	NPC472224
0.9222	High Similarity	NPC472223
0.8587	High Similarity	NPC150383
0.8571	High Similarity	NPC473039
0.8295	Intermediate Similarity	NPC472229
0.8295	Intermediate Similarity	NPC472230
0.82	Intermediate Similarity	NPC472227
0.82	Intermediate Similarity	NPC472228
0.8172	Intermediate Similarity	NPC305039
0.8111	Intermediate Similarity	NPC271784
0.8111	Intermediate Similarity	NPC469561
0.8065	Intermediate Similarity	NPC28227
0.802	Intermediate Similarity	NPC119493
0.8	Intermediate Similarity	NPC321289
0.8	Intermediate Similarity	NPC327969
0.7959	Intermediate Similarity	NPC187159
0.7935	Intermediate Similarity	NPC470223
0.7857	Intermediate Similarity	NPC322063
0.7849	Intermediate Similarity	NPC195640
0.7843	Intermediate Similarity	NPC164835
0.7843	Intermediate Similarity	NPC228669
0.7826	Intermediate Similarity	NPC209882
0.7826	Intermediate Similarity	NPC320801
0.7826	Intermediate Similarity	NPC100391
0.7789	Intermediate Similarity	NPC54689
0.7767	Intermediate Similarity	NPC127790
0.7742	Intermediate Similarity	NPC473038
0.7742	Intermediate Similarity	NPC323765
0.7732	Intermediate Similarity	NPC25750
0.7732	Intermediate Similarity	NPC243866
0.7717	Intermediate Similarity	NPC168188
0.7717	Intermediate Similarity	NPC470015
0.7677	Intermediate Similarity	NPC125622
0.7667	Intermediate Similarity	NPC118987
0.7653	Intermediate Similarity	NPC294266
0.7653	Intermediate Similarity	NPC56525
0.7647	Intermediate Similarity	NPC56498
0.7634	Intermediate Similarity	NPC109512
0.7629	Intermediate Similarity	NPC154101
0.7624	Intermediate Similarity	NPC205899
0.7609	Intermediate Similarity	NPC100297
0.7609	Intermediate Similarity	NPC240302
0.76	Intermediate Similarity	NPC18319
0.76	Intermediate Similarity	NPC475894
0.76	Intermediate Similarity	NPC476253
0.7582	Intermediate Similarity	NPC474956
0.7582	Intermediate Similarity	NPC170038
0.7579	Intermediate Similarity	NPC167877
0.7579	Intermediate Similarity	NPC136948
0.7576	Intermediate Similarity	NPC184848
0.7576	Intermediate Similarity	NPC241156
0.7576	Intermediate Similarity	NPC69548
0.7576	Intermediate Similarity	NPC171395
0.7573	Intermediate Similarity	NPC36321
0.7556	Intermediate Similarity	NPC469996
0.7553	Intermediate Similarity	NPC94531
0.7553	Intermediate Similarity	NPC123319
0.7553	Intermediate Similarity	NPC311702
0.7551	Intermediate Similarity	NPC66429
0.7551	Intermediate Similarity	NPC152897
0.7525	Intermediate Similarity	NPC10364
0.7525	Intermediate Similarity	NPC153792
0.7525	Intermediate Similarity	NPC176845
0.7525	Intermediate Similarity	NPC271387
0.7523	Intermediate Similarity	NPC471398
0.75	Intermediate Similarity	NPC38350
0.75	Intermediate Similarity	NPC183546
0.75	Intermediate Similarity	NPC155676
0.75	Intermediate Similarity	NPC201912
0.75	Intermediate Similarity	NPC294480
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC95565
0.75	Intermediate Similarity	NPC232625
0.7477	Intermediate Similarity	NPC163314
0.7476	Intermediate Similarity	NPC22388
0.7475	Intermediate Similarity	NPC184870
0.7474	Intermediate Similarity	NPC212843
0.7474	Intermediate Similarity	NPC244174
0.7449	Intermediate Similarity	NPC204341
0.7449	Intermediate Similarity	NPC23434
0.7447	Intermediate Similarity	NPC120158
0.7447	Intermediate Similarity	NPC475193
0.7447	Intermediate Similarity	NPC469407
0.7429	Intermediate Similarity	NPC470309
0.7426	Intermediate Similarity	NPC107243
0.7426	Intermediate Similarity	NPC23680
0.7426	Intermediate Similarity	NPC216904
0.7426	Intermediate Similarity	NPC121339
0.7426	Intermediate Similarity	NPC57416
0.7426	Intermediate Similarity	NPC292133
0.7423	Intermediate Similarity	NPC215029
0.7423	Intermediate Similarity	NPC155479
0.7423	Intermediate Similarity	NPC472234
0.7423	Intermediate Similarity	NPC476733
0.7423	Intermediate Similarity	NPC262043
0.7423	Intermediate Similarity	NPC173042
0.7423	Intermediate Similarity	NPC285982
0.7423	Intermediate Similarity	NPC472233
0.7419	Intermediate Similarity	NPC258153
0.7419	Intermediate Similarity	NPC320514
0.7419	Intermediate Similarity	NPC260956
0.7419	Intermediate Similarity	NPC193347
0.7419	Intermediate Similarity	NPC133391
0.7419	Intermediate Similarity	NPC476458
0.7404	Intermediate Similarity	NPC236390
0.7404	Intermediate Similarity	NPC140723
0.74	Intermediate Similarity	NPC469599
0.74	Intermediate Similarity	NPC263347
0.7396	Intermediate Similarity	NPC265580
0.7396	Intermediate Similarity	NPC312215
0.7379	Intermediate Similarity	NPC99411
0.7374	Intermediate Similarity	NPC470576
0.7368	Intermediate Similarity	NPC29447
0.7368	Intermediate Similarity	NPC11711
0.7358	Intermediate Similarity	NPC473037
0.7358	Intermediate Similarity	NPC220974
0.7353	Intermediate Similarity	NPC275439
0.7353	Intermediate Similarity	NPC477813
0.7353	Intermediate Similarity	NPC112753
0.7347	Intermediate Similarity	NPC478257
0.7347	Intermediate Similarity	NPC478258
0.734	Intermediate Similarity	NPC477373
0.734	Intermediate Similarity	NPC83569
0.734	Intermediate Similarity	NPC472492
0.734	Intermediate Similarity	NPC69279
0.7333	Intermediate Similarity	NPC28656
0.7327	Intermediate Similarity	NPC42042
0.7327	Intermediate Similarity	NPC7124
0.7327	Intermediate Similarity	NPC3772
0.7315	Intermediate Similarity	NPC473036
0.7315	Intermediate Similarity	NPC272898
0.7315	Intermediate Similarity	NPC27551
0.7315	Intermediate Similarity	NPC114961
0.7312	Intermediate Similarity	NPC150506
0.7312	Intermediate Similarity	NPC147066
0.7308	Intermediate Similarity	NPC308351
0.7308	Intermediate Similarity	NPC271266
0.7308	Intermediate Similarity	NPC204450
0.7308	Intermediate Similarity	NPC195290
0.73	Intermediate Similarity	NPC471720
0.729	Intermediate Similarity	NPC61411
0.729	Intermediate Similarity	NPC469844
0.7283	Intermediate Similarity	NPC477371
0.7282	Intermediate Similarity	NPC307954
0.7273	Intermediate Similarity	NPC179517
0.7273	Intermediate Similarity	NPC474631
0.7273	Intermediate Similarity	NPC197701
0.7273	Intermediate Similarity	NPC190442
0.7273	Intermediate Similarity	NPC65513
0.7273	Intermediate Similarity	NPC165904
0.7273	Intermediate Similarity	NPC223187
0.7273	Intermediate Similarity	NPC218301
0.7273	Intermediate Similarity	NPC178981
0.7263	Intermediate Similarity	NPC71626
0.7263	Intermediate Similarity	NPC144258
0.7257	Intermediate Similarity	NPC474179
0.7257	Intermediate Similarity	NPC475834
0.7255	Intermediate Similarity	NPC204054
0.7255	Intermediate Similarity	NPC257726
0.7255	Intermediate Similarity	NPC106557
0.7253	Intermediate Similarity	NPC472300
0.7248	Intermediate Similarity	NPC470577
0.7245	Intermediate Similarity	NPC474570
0.7245	Intermediate Similarity	NPC474679
0.7245	Intermediate Similarity	NPC477943
0.7245	Intermediate Similarity	NPC474889
0.7238	Intermediate Similarity	NPC55872
0.7228	Intermediate Similarity	NPC470016
0.7228	Intermediate Similarity	NPC45324
0.7228	Intermediate Similarity	NPC473648
0.7228	Intermediate Similarity	NPC162001
0.7228	Intermediate Similarity	NPC317586
0.7228	Intermediate Similarity	NPC255809
0.7228	Intermediate Similarity	NPC37646
0.7228	Intermediate Similarity	NPC222845
0.7228	Intermediate Similarity	NPC280877
0.7222	Intermediate Similarity	NPC304495
0.7216	Intermediate Similarity	NPC99909
0.7212	Intermediate Similarity	NPC124211
0.7212	Intermediate Similarity	NPC474327
0.7203	Intermediate Similarity	NPC473888
0.72	Intermediate Similarity	NPC470375
0.72	Intermediate Similarity	NPC472232
0.72	Intermediate Similarity	NPC229976
0.72	Intermediate Similarity	NPC475700
0.72	Intermediate Similarity	NPC472237
0.72	Intermediate Similarity	NPC267266
0.72	Intermediate Similarity	NPC206810
0.72	Intermediate Similarity	NPC277721
0.72	Intermediate Similarity	NPC472231
0.72	Intermediate Similarity	NPC470224
0.72	Intermediate Similarity	NPC472238
0.72	Intermediate Similarity	NPC470376
0.72	Intermediate Similarity	NPC470254
0.7188	Intermediate Similarity	NPC300985
0.7184	Intermediate Similarity	NPC186810
0.7184	Intermediate Similarity	NPC166745
0.7184	Intermediate Similarity	NPC197386
0.7184	Intermediate Similarity	NPC235464

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 NPC472225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	2549
0.2-0.3	4338
0.3-0.4	1356
0.4-0.5	316
0.5-0.6	188
0.6-0.7	121
0.7-0.8	36
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD5207	Approved
0.8316	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD6050	Approved
0.8172	Intermediate Similarity	NPD6080	Approved
0.8172	Intermediate Similarity	NPD6673	Approved
0.8172	Intermediate Similarity	NPD6904	Approved
0.8085	Intermediate Similarity	NPD5692	Phase 3
0.8021	Intermediate Similarity	NPD6001	Approved
0.8	Intermediate Similarity	NPD5694	Approved
0.8	Intermediate Similarity	NPD5284	Approved
0.8	Intermediate Similarity	NPD5281	Approved
0.7872	Intermediate Similarity	NPD5208	Approved
0.7872	Intermediate Similarity	NPD6903	Approved
0.7849	Intermediate Similarity	NPD7521	Approved
0.7849	Intermediate Similarity	NPD7334	Approved
0.7849	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD7146	Approved
0.7849	Intermediate Similarity	NPD6409	Approved
0.7849	Intermediate Similarity	NPD5330	Approved
0.7849	Intermediate Similarity	NPD6098	Approved
0.7812	Intermediate Similarity	NPD5693	Phase 1
0.7755	Intermediate Similarity	NPD5654	Approved
0.7755	Intermediate Similarity	NPD5695	Phase 3
0.7745	Intermediate Similarity	NPD6052	Approved
0.7684	Intermediate Similarity	NPD6672	Approved
0.7684	Intermediate Similarity	NPD5737	Approved
0.7684	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6083	Phase 2
0.76	Intermediate Similarity	NPD6084	Phase 2
0.76	Intermediate Similarity	NPD5959	Approved
0.7596	Intermediate Similarity	NPD6008	Approved
0.7525	Intermediate Similarity	NPD5696	Approved
0.7419	Intermediate Similarity	NPD4223	Phase 3
0.7419	Intermediate Similarity	NPD4221	Approved
0.7374	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD5329	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.7312	Intermediate Similarity	NPD4692	Approved
0.7312	Intermediate Similarity	NPD4139	Approved
0.7292	Intermediate Similarity	NPD5690	Phase 2
0.7292	Intermediate Similarity	NPD4694	Approved
0.7292	Intermediate Similarity	NPD5280	Approved
0.729	Intermediate Similarity	NPD7320	Approved
0.7264	Intermediate Similarity	NPD6675	Approved
0.7264	Intermediate Similarity	NPD7128	Approved
0.7264	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD5739	Approved
0.7263	Intermediate Similarity	NPD4197	Approved
0.7222	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD6373	Approved
0.7196	Intermediate Similarity	NPD6614	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.7113	Intermediate Similarity	NPD4688	Approved
0.7113	Intermediate Similarity	NPD4690	Approved
0.7113	Intermediate Similarity	NPD5205	Approved
0.7113	Intermediate Similarity	NPD4689	Approved
0.7113	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4138	Approved
0.7113	Intermediate Similarity	NPD4693	Phase 3
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6649	Approved
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7037	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD5701	Approved
0.7037	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6989	Remote Similarity	NPD3617	Approved
0.6975	Remote Similarity	NPD7078	Approved
0.6972	Remote Similarity	NPD6011	Approved
0.6961	Remote Similarity	NPD7900	Approved
0.6961	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7492	Approved
0.6937	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6869	Approved
0.6937	Remote Similarity	NPD8130	Phase 1
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5733	Approved
0.6909	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD6014	Approved
0.6909	Remote Similarity	NPD6013	Approved
0.6907	Remote Similarity	NPD3666	Approved
0.6907	Remote Similarity	NPD3133	Approved
0.6907	Remote Similarity	NPD3665	Phase 1
0.6897	Remote Similarity	NPD6054	Approved
0.6897	Remote Similarity	NPD6059	Approved
0.6893	Remote Similarity	NPD5210	Approved
0.6893	Remote Similarity	NPD4629	Approved
0.6891	Remote Similarity	NPD6616	Approved
0.6875	Remote Similarity	NPD8297	Approved
0.6869	Remote Similarity	NPD3573	Approved
0.6863	Remote Similarity	NPD4202	Approved
0.6863	Remote Similarity	NPD5133	Approved
0.6833	Remote Similarity	NPD8293	Discontinued
0.6832	Remote Similarity	NPD4096	Approved
0.6783	Remote Similarity	NPD6009	Approved
0.678	Remote Similarity	NPD6370	Approved
0.6778	Remote Similarity	NPD4747	Approved
0.6777	Remote Similarity	NPD7736	Approved
0.6762	Remote Similarity	NPD4755	Approved
0.6762	Remote Similarity	NPD7902	Approved
0.6739	Remote Similarity	NPD4687	Approved
0.6737	Remote Similarity	NPD4195	Approved
0.6733	Remote Similarity	NPD6051	Approved
0.6733	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5777	Approved
0.6703	Remote Similarity	NPD5276	Approved
0.6695	Remote Similarity	NPD6016	Approved
0.6695	Remote Similarity	NPD6015	Approved
0.6695	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6639	Remote Similarity	NPD5988	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6635	Remote Similarity	NPD7748	Approved
0.6634	Remote Similarity	NPD4518	Approved
0.6633	Remote Similarity	NPD4788	Approved
0.6602	Remote Similarity	NPD8035	Phase 2
0.6602	Remote Similarity	NPD8034	Phase 2
0.66	Remote Similarity	NPD3618	Phase 1
0.66	Remote Similarity	NPD5279	Phase 3
0.6593	Remote Similarity	NPD4691	Approved
0.6581	Remote Similarity	NPD6335	Approved
0.6574	Remote Similarity	NPD5223	Approved
0.6569	Remote Similarity	NPD5328	Approved
0.6566	Remote Similarity	NPD4786	Approved
0.6552	Remote Similarity	NPD6274	Approved
0.6531	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7100	Approved
0.6525	Remote Similarity	NPD7101	Approved
0.6522	Remote Similarity	NPD4632	Approved
0.6514	Remote Similarity	NPD5091	Approved
0.6514	Remote Similarity	NPD5225	Approved
0.6514	Remote Similarity	NPD5211	Phase 2
0.6514	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD4633	Approved
0.6514	Remote Similarity	NPD5224	Approved
0.6509	Remote Similarity	NPD7732	Phase 3
0.6504	Remote Similarity	NPD6033	Approved
0.6496	Remote Similarity	NPD6317	Approved
0.6489	Remote Similarity	NPD3702	Approved
0.6475	Remote Similarity	NPD7507	Approved
0.646	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4754	Approved
0.6455	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD5175	Approved
0.6446	Remote Similarity	NPD6067	Discontinued
0.6442	Remote Similarity	NPD6079	Approved
0.6442	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD6314	Approved
0.6441	Remote Similarity	NPD6313	Approved
0.6435	Remote Similarity	NPD6053	Discontinued
0.6417	Remote Similarity	NPD6909	Approved
0.6417	Remote Similarity	NPD6908	Approved
0.64	Remote Similarity	NPD3668	Phase 3
0.6396	Remote Similarity	NPD5141	Approved
0.6389	Remote Similarity	NPD7638	Approved
0.6383	Remote Similarity	NPD4058	Approved
0.6364	Remote Similarity	NPD3667	Approved
0.6356	Remote Similarity	NPD7115	Discovery
0.6355	Remote Similarity	NPD4697	Phase 3
0.6355	Remote Similarity	NPD7614	Phase 1
0.6344	Remote Similarity	NPD4243	Approved
0.6344	Remote Similarity	NPD6081	Approved
0.6339	Remote Similarity	NPD4768	Approved
0.6339	Remote Similarity	NPD4767	Approved
0.6333	Remote Similarity	NPD6319	Approved
0.633	Remote Similarity	NPD7639	Approved
0.633	Remote Similarity	NPD7640	Approved
0.633	Remote Similarity	NPD6404	Discontinued
0.6327	Remote Similarity	NPD4695	Discontinued
0.632	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD7604	Phase 2
0.6283	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5983	Phase 2
0.6275	Remote Similarity	NPD4519	Discontinued
0.6275	Remote Similarity	NPD4623	Approved
0.627	Remote Similarity	NPD5956	Approved
0.6239	Remote Similarity	NPD6858	Approved
0.6239	Remote Similarity	NPD7094	Approved
0.6228	Remote Similarity	NPD4729	Approved
0.6228	Remote Similarity	NPD4730	Approved
0.6228	Remote Similarity	NPD5128	Approved
0.6228	Remote Similarity	NPD6686	Approved
0.6216	Remote Similarity	NPD7632	Discontinued
0.6211	Remote Similarity	NPD4785	Approved
0.6211	Remote Similarity	NPD4784	Approved
0.621	Remote Similarity	NPD6336	Discontinued
0.6204	Remote Similarity	NPD5221	Approved
0.6204	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5222	Approved
0.6196	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5707	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