NPASS Compound

Structure

NPC167877 OpenBabel07101718232D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9449 -2.7499 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 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.7321 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 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 -0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2812 -2.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2757 -2.0068 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8745 -1.1977 0.0000 C 0 0 2 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 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 -2.2321 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4837 -1.0286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -3.2321 -4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3972 -0.6219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6176 -0.5286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 25 2 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 27 1 0 0 0 0 21 16 1 1 0 0 0 21 34 1 0 0 0 0 22 28 1 6 0 0 0 23 29 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 1 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	517.825
LogP:	6.249
LogD:	4.932
LogS:	-6.092
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	5.062
Fsp3:	0.8
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:	-5.045
MDCK Permeability:	1.5005960449343547e-05
Pgp-inhibitor:	0.232
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.165
Plasma Protein Binding (PPB):	97.11341094970703%
Volume Distribution (VD):	0.657
Pgp-substrate:	3.347625494003296%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.416
CYP3A4-inhibitor:	0.486
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	3.987
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.61
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.516
Carcinogencity:	0.211
Eye Corrosion:	0.517
Eye Irritation:	0.089
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC167877

Natural Product ID:	NPC167877
*Common Name:**	(23R,25R)-3,4-Seco-9Beta-H-Lanosta-4(28),7-Dien-26,23-Olid-3-Oic Acid
IUPAC Name:	3-[(3R,3aR,5aS,6S,7S,9bR)-3a,6,9b-trimethyl-3-[(2R)-1-[(2R,4R)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-7-prop-1-en-2-yl-1,2,3,4,5,5a,7,8-octahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
Synonyms:
Standard InCHIKey:	ZDQKZDFYRZDVIL-XLPYTDSASA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(2)22-8-9-25-24(28(22,5)13-12-26(31)32)11-15-29(6)23(10-14-30(25,29)7)19(3)16-21-17-20(4)27(33)34-21/h9,19-24H,1,8,10-17H2,2-7H3,(H,31,32)/t19-,20-,21-,22+,23-,24-,28+,29-,30+/m1/s1
SMILES:	OC(=O)CC[C@@]1(C)[C@@H](CC=C2[C@H]1CC[C@]1([C@@]2(C)CC[C@@H]1[C@@H](C[C@@H]1C[C@H](C(=O)O1)C)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462847
PubChem CID:	21602071
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23553	Abies sachalinensis	Species	Pinaceae	Eukaryota	Barks	n.a.	n.a.	PMID[12444693]
NPO23553	Abies sachalinensis	Species	Pinaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	42600.0	nM	PMID[534763]

☑ 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 NPC167877 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	163
0.1-0.2	968
0.2-0.3	5308
0.3-0.4	15036
0.4-0.5	7048
0.5-0.6	6057
0.6-0.7	6202
0.7-0.8	1755
0.8-0.85	133
0.85-0.9	24
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC100391
0.9195	High Similarity	NPC470224
0.9048	High Similarity	NPC470223
0.9	High Similarity	NPC475894
0.8966	High Similarity	NPC471896
0.8966	High Similarity	NPC111585
0.8966	High Similarity	NPC148414
0.8966	High Similarity	NPC175628
0.8953	High Similarity	NPC28227
0.8953	High Similarity	NPC294480
0.8929	High Similarity	NPC165064
0.8916	High Similarity	NPC133391
0.8864	High Similarity	NPC154101
0.8864	High Similarity	NPC26888
0.8864	High Similarity	NPC150383
0.8851	High Similarity	NPC474889
0.8851	High Similarity	NPC474570
0.8837	High Similarity	NPC312215
0.8795	High Similarity	NPC327002
0.8795	High Similarity	NPC232625
0.878	High Similarity	NPC327674
0.878	High Similarity	NPC477371
0.8778	High Similarity	NPC469599
0.8736	High Similarity	NPC183546
0.8721	High Similarity	NPC212843
0.8721	High Similarity	NPC155011
0.869	High Similarity	NPC240302
0.8681	High Similarity	NPC322063
0.8675	High Similarity	NPC170038
0.8667	High Similarity	NPC159410
0.8659	High Similarity	NPC321514
0.8652	High Similarity	NPC297265
0.8636	High Similarity	NPC54689
0.8636	High Similarity	NPC475921
0.8636	High Similarity	NPC474704
0.8621	High Similarity	NPC96496
0.8621	High Similarity	NPC187376
0.8621	High Similarity	NPC474684
0.8621	High Similarity	NPC159046
0.8621	High Similarity	NPC233836
0.8621	High Similarity	NPC142361
0.8605	High Similarity	NPC329738
0.8602	High Similarity	NPC476303
0.8588	High Similarity	NPC477373
0.8588	High Similarity	NPC470948
0.8571	High Similarity	NPC69548
0.8571	High Similarity	NPC38350
0.8571	High Similarity	NPC184848
0.8571	High Similarity	NPC477372
0.8571	High Similarity	NPC147066
0.8571	High Similarity	NPC201912
0.8556	High Similarity	NPC470376
0.8556	High Similarity	NPC170220
0.8556	High Similarity	NPC107674
0.8556	High Similarity	NPC152897
0.8556	High Similarity	NPC66429
0.8556	High Similarity	NPC141497
0.8556	High Similarity	NPC470375
0.8554	High Similarity	NPC118987
0.8539	High Similarity	NPC46281
0.8539	High Similarity	NPC44240
0.8539	High Similarity	NPC123854
0.8526	High Similarity	NPC140723
0.8523	High Similarity	NPC229407
0.8523	High Similarity	NPC250687
0.8523	High Similarity	NPC48866
0.8523	High Similarity	NPC242864
0.8523	High Similarity	NPC254572
0.8523	High Similarity	NPC48824
0.8523	High Similarity	NPC247406
0.8506	High Similarity	NPC28252
0.8506	High Similarity	NPC55309
0.8506	High Similarity	NPC6979
0.8506	High Similarity	NPC264127
0.8495	Intermediate Similarity	NPC271387
0.8495	Intermediate Similarity	NPC477813
0.8495	Intermediate Similarity	NPC153792
0.8471	Intermediate Similarity	NPC296367
0.8471	Intermediate Similarity	NPC260956
0.8462	Intermediate Similarity	NPC471720
0.8444	Intermediate Similarity	NPC212301
0.8444	Intermediate Similarity	NPC23434
0.8444	Intermediate Similarity	NPC86266
0.8444	Intermediate Similarity	NPC110657
0.8444	Intermediate Similarity	NPC189520
0.8438	Intermediate Similarity	NPC471293
0.8438	Intermediate Similarity	NPC255309
0.8438	Intermediate Similarity	NPC472227
0.8438	Intermediate Similarity	NPC472228
0.8434	Intermediate Similarity	NPC35574
0.8427	Intermediate Similarity	NPC102414
0.8427	Intermediate Similarity	NPC155479
0.8427	Intermediate Similarity	NPC269267
0.8427	Intermediate Similarity	NPC77168
0.8427	Intermediate Similarity	NPC84271
0.8427	Intermediate Similarity	NPC476733
0.8427	Intermediate Similarity	NPC215029
0.8409	Intermediate Similarity	NPC128644
0.8404	Intermediate Similarity	NPC476274
0.8391	Intermediate Similarity	NPC283733
0.8391	Intermediate Similarity	NPC52628
0.8391	Intermediate Similarity	NPC474218
0.8387	Intermediate Similarity	NPC57416
0.8387	Intermediate Similarity	NPC107243
0.8372	Intermediate Similarity	NPC83569
0.8372	Intermediate Similarity	NPC471037
0.8372	Intermediate Similarity	NPC167103
0.8372	Intermediate Similarity	NPC69279
0.837	Intermediate Similarity	NPC263347
0.837	Intermediate Similarity	NPC222845
0.837	Intermediate Similarity	NPC45324
0.837	Intermediate Similarity	NPC279974
0.837	Intermediate Similarity	NPC162001
0.8352	Intermediate Similarity	NPC474436
0.8352	Intermediate Similarity	NPC63118
0.8352	Intermediate Similarity	NPC243866
0.8352	Intermediate Similarity	NPC49776
0.8351	Intermediate Similarity	NPC96377
0.8333	Intermediate Similarity	NPC196827
0.8333	Intermediate Similarity	NPC36688
0.8333	Intermediate Similarity	NPC477147
0.8333	Intermediate Similarity	NPC477149
0.8333	Intermediate Similarity	NPC274996
0.8333	Intermediate Similarity	NPC476237
0.8333	Intermediate Similarity	NPC158846
0.8333	Intermediate Similarity	NPC469400
0.8333	Intermediate Similarity	NPC176883
0.8316	Intermediate Similarity	NPC474327
0.8316	Intermediate Similarity	NPC224720
0.8316	Intermediate Similarity	NPC476240
0.8316	Intermediate Similarity	NPC476223
0.8315	Intermediate Similarity	NPC472220
0.8315	Intermediate Similarity	NPC226863
0.8315	Intermediate Similarity	NPC97884
0.8295	Intermediate Similarity	NPC470051
0.8295	Intermediate Similarity	NPC470050
0.8295	Intermediate Similarity	NPC73038
0.8295	Intermediate Similarity	NPC325594
0.8295	Intermediate Similarity	NPC474970
0.8295	Intermediate Similarity	NPC195640
0.828	Intermediate Similarity	NPC327788
0.828	Intermediate Similarity	NPC42042
0.828	Intermediate Similarity	NPC120708
0.828	Intermediate Similarity	NPC307164
0.828	Intermediate Similarity	NPC155676
0.8276	Intermediate Similarity	NPC59453
0.8276	Intermediate Similarity	NPC214043
0.8276	Intermediate Similarity	NPC476038
0.8276	Intermediate Similarity	NPC164577
0.8276	Intermediate Similarity	NPC194937
0.8276	Intermediate Similarity	NPC221758
0.8276	Intermediate Similarity	NPC473246
0.8276	Intermediate Similarity	NPC85774
0.8276	Intermediate Similarity	NPC82902
0.8265	Intermediate Similarity	NPC220974
0.8265	Intermediate Similarity	NPC59530
0.8261	Intermediate Similarity	NPC124207
0.8261	Intermediate Similarity	NPC49670
0.8261	Intermediate Similarity	NPC7165
0.8261	Intermediate Similarity	NPC56525
0.8261	Intermediate Similarity	NPC469406
0.8256	Intermediate Similarity	NPC320514
0.8242	Intermediate Similarity	NPC45269
0.8242	Intermediate Similarity	NPC471747
0.8242	Intermediate Similarity	NPC470113
0.8235	Intermediate Similarity	NPC104545
0.8222	Intermediate Similarity	NPC128496
0.8222	Intermediate Similarity	NPC474679
0.8222	Intermediate Similarity	NPC477943
0.8222	Intermediate Similarity	NPC214387
0.8211	Intermediate Similarity	NPC167974
0.8211	Intermediate Similarity	NPC218383
0.8202	Intermediate Similarity	NPC136948
0.8202	Intermediate Similarity	NPC317590
0.8202	Intermediate Similarity	NPC90652
0.8193	Intermediate Similarity	NPC41017
0.8193	Intermediate Similarity	NPC476601
0.8182	Intermediate Similarity	NPC269638
0.8182	Intermediate Similarity	NPC29447
0.8182	Intermediate Similarity	NPC471224
0.8182	Intermediate Similarity	NPC474083
0.8182	Intermediate Similarity	NPC323765
0.8172	Intermediate Similarity	NPC20546
0.8172	Intermediate Similarity	NPC473648
0.8172	Intermediate Similarity	NPC317586
0.8172	Intermediate Similarity	NPC470016
0.8161	Intermediate Similarity	NPC278648
0.8161	Intermediate Similarity	NPC168188
0.8161	Intermediate Similarity	NPC97913
0.8161	Intermediate Similarity	NPC476082
0.8161	Intermediate Similarity	NPC470015
0.8161	Intermediate Similarity	NPC310470
0.8152	Intermediate Similarity	NPC267266
0.8152	Intermediate Similarity	NPC470656
0.8152	Intermediate Similarity	NPC470254
0.8152	Intermediate Similarity	NPC206810
0.8152	Intermediate Similarity	NPC277721
0.8148	Intermediate Similarity	NPC160817
0.814	Intermediate Similarity	NPC475665
0.814	Intermediate Similarity	NPC14203

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 NPC167877 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1362
0.2-0.3	4069
0.3-0.4	2442
0.4-0.5	621
0.5-0.6	206
0.6-0.7	196
0.7-0.8	116
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8977	High Similarity	NPD6399	Phase 3
0.8315	Intermediate Similarity	NPD6672	Approved
0.8315	Intermediate Similarity	NPD6903	Approved
0.8315	Intermediate Similarity	NPD5737	Approved
0.8295	Intermediate Similarity	NPD7334	Approved
0.8295	Intermediate Similarity	NPD6409	Approved
0.8295	Intermediate Similarity	NPD6684	Approved
0.8295	Intermediate Similarity	NPD7521	Approved
0.8295	Intermediate Similarity	NPD7146	Approved
0.8295	Intermediate Similarity	NPD5330	Approved
0.8276	Intermediate Similarity	NPD4786	Approved
0.8191	Intermediate Similarity	NPD6083	Phase 2
0.8191	Intermediate Similarity	NPD6084	Phase 2
0.8172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD5695	Phase 3
0.8111	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD5696	Approved
0.8046	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD8035	Phase 2
0.8043	Intermediate Similarity	NPD8034	Phase 2
0.7935	Intermediate Similarity	NPD5207	Approved
0.7889	Intermediate Similarity	NPD3618	Phase 1
0.7889	Intermediate Similarity	NPD6098	Approved
0.7872	Intermediate Similarity	NPD7748	Approved
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7849	Intermediate Similarity	NPD5281	Approved
0.7849	Intermediate Similarity	NPD5284	Approved
0.7826	Intermediate Similarity	NPD6080	Approved
0.7826	Intermediate Similarity	NPD6904	Approved
0.7826	Intermediate Similarity	NPD5328	Approved
0.7826	Intermediate Similarity	NPD6673	Approved
0.7822	Intermediate Similarity	NPD7320	Approved
0.7812	Intermediate Similarity	NPD7902	Approved
0.78	Intermediate Similarity	NPD5739	Approved
0.78	Intermediate Similarity	NPD7128	Approved
0.78	Intermediate Similarity	NPD6675	Approved
0.78	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6372	Approved
0.7745	Intermediate Similarity	NPD6373	Approved
0.7692	Intermediate Similarity	NPD5279	Phase 3
0.7684	Intermediate Similarity	NPD6001	Approved
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.766	Intermediate Similarity	NPD6050	Approved
0.766	Intermediate Similarity	NPD7515	Phase 2
0.766	Intermediate Similarity	NPD6079	Approved
0.7647	Intermediate Similarity	NPD6899	Approved
0.7647	Intermediate Similarity	NPD6881	Approved
0.764	Intermediate Similarity	NPD4223	Phase 3
0.764	Intermediate Similarity	NPD4221	Approved
0.7634	Intermediate Similarity	NPD4753	Phase 2
0.7624	Intermediate Similarity	NPD6008	Approved
0.7596	Intermediate Similarity	NPD6649	Approved
0.7596	Intermediate Similarity	NPD6650	Approved
0.7586	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5329	Approved
0.7556	Intermediate Similarity	NPD5362	Discontinued
0.7553	Intermediate Similarity	NPD5692	Phase 3
0.7551	Intermediate Similarity	NPD7638	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7549	Intermediate Similarity	NPD5697	Approved
0.7527	Intermediate Similarity	NPD5208	Approved
0.7526	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7476	Intermediate Similarity	NPD6011	Approved
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7474	Intermediate Similarity	NPD5693	Phase 1
0.7474	Intermediate Similarity	NPD5694	Approved
0.7474	Intermediate Similarity	NPD6411	Approved
0.7473	Intermediate Similarity	NPD4197	Approved
0.7447	Intermediate Similarity	NPD6051	Approved
0.7444	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7339	Approved
0.7442	Intermediate Similarity	NPD6942	Approved
0.7429	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8130	Phase 1
0.7429	Intermediate Similarity	NPD6869	Approved
0.7429	Intermediate Similarity	NPD6617	Approved
0.7429	Intermediate Similarity	NPD6847	Approved
0.7426	Intermediate Similarity	NPD6052	Approved
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7404	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD6013	Approved
0.7404	Intermediate Similarity	NPD6014	Approved
0.7396	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD1694	Approved
0.7358	Intermediate Similarity	NPD6882	Approved
0.7358	Intermediate Similarity	NPD8297	Approved
0.7347	Intermediate Similarity	NPD5221	Approved
0.7347	Intermediate Similarity	NPD5222	Approved
0.7347	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5369	Approved
0.7312	Intermediate Similarity	NPD5690	Phase 2
0.7312	Intermediate Similarity	NPD4689	Approved
0.7312	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4694	Approved
0.7312	Intermediate Similarity	NPD4688	Approved
0.7312	Intermediate Similarity	NPD4693	Phase 3
0.7312	Intermediate Similarity	NPD4138	Approved
0.7312	Intermediate Similarity	NPD5280	Approved
0.7312	Intermediate Similarity	NPD5205	Approved
0.7312	Intermediate Similarity	NPD4690	Approved
0.7292	Intermediate Similarity	NPD7637	Suspended
0.7273	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD5173	Approved
0.7263	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6101	Approved
0.7253	Intermediate Similarity	NPD6435	Approved
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7222	Intermediate Similarity	NPD7525	Registered
0.7212	Intermediate Similarity	NPD6412	Phase 2
0.7204	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3617	Approved
0.7174	Intermediate Similarity	NPD4788	Approved
0.7159	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6117	Approved
0.7156	Intermediate Similarity	NPD6868	Approved
0.7143	Intermediate Similarity	NPD4692	Approved
0.7143	Intermediate Similarity	NPD4139	Approved
0.7143	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5286	Approved
0.7129	Intermediate Similarity	NPD4700	Approved
0.7129	Intermediate Similarity	NPD4696	Approved
0.7129	Intermediate Similarity	NPD5285	Approved
0.7126	Intermediate Similarity	NPD6926	Approved
0.7126	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6924	Approved
0.7093	Intermediate Similarity	NPD4243	Approved
0.7083	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6116	Phase 1
0.7071	Intermediate Similarity	NPD5654	Approved
0.7065	Intermediate Similarity	NPD4270	Approved
0.7065	Intermediate Similarity	NPD4269	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7045	Intermediate Similarity	NPD3702	Approved
0.7041	Intermediate Similarity	NPD5778	Approved
0.7041	Intermediate Similarity	NPD5779	Approved
0.7037	Intermediate Similarity	NPD6053	Discontinued
0.7033	Intermediate Similarity	NPD5368	Approved
0.7033	Intermediate Similarity	NPD4695	Discontinued
0.703	Intermediate Similarity	NPD4225	Approved
0.7027	Intermediate Similarity	NPD6335	Approved
0.701	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD6118	Approved
0.7	Intermediate Similarity	NPD6697	Approved
0.7	Intermediate Similarity	NPD6115	Approved
0.699	Remote Similarity	NPD5225	Approved
0.699	Remote Similarity	NPD5226	Approved
0.699	Remote Similarity	NPD4633	Approved
0.699	Remote Similarity	NPD5224	Approved
0.699	Remote Similarity	NPD5211	Phase 2
0.6989	Remote Similarity	NPD7154	Phase 3
0.6989	Remote Similarity	NPD6695	Phase 3
0.6989	Remote Similarity	NPD5331	Approved
0.6989	Remote Similarity	NPD5332	Approved
0.6977	Remote Similarity	NPD4747	Approved
0.6972	Remote Similarity	NPD4632	Approved
0.6966	Remote Similarity	NPD6933	Approved
0.6964	Remote Similarity	NPD7101	Approved
0.6964	Remote Similarity	NPD7100	Approved
0.6961	Remote Similarity	NPD6404	Discontinued
0.6957	Remote Similarity	NPD4790	Discontinued
0.6957	Remote Similarity	NPD7492	Approved
0.6947	Remote Similarity	NPD5786	Approved
0.6937	Remote Similarity	NPD6317	Approved
0.6932	Remote Similarity	NPD5733	Approved
0.6932	Remote Similarity	NPD4785	Approved
0.6932	Remote Similarity	NPD4784	Approved
0.6931	Remote Similarity	NPD5959	Approved
0.6923	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD5175	Approved
0.6923	Remote Similarity	NPD5174	Approved
0.6923	Remote Similarity	NPD4754	Approved
0.6915	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6054	Approved
0.6903	Remote Similarity	NPD6059	Approved
0.69	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5777	Approved
0.6897	Remote Similarity	NPD6081	Approved
0.6897	Remote Similarity	NPD6616	Approved
0.6887	Remote Similarity	NPD6614	Approved
0.6875	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD6314	Approved
0.6875	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD7122	Discontinued
0.686	Remote Similarity	NPD6922	Approved
0.686	Remote Similarity	NPD4137	Phase 3
0.686	Remote Similarity	NPD6923	Approved
0.6857	Remote Similarity	NPD5141	Approved
0.6854	Remote Similarity	NPD8039	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