NPASS Compound

Structure

NPC475772 OpenBabel07101718272D 32 35 0 0 1 0 0 0 0 0999 V2000 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 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 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 3.0032 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 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 -4.3301 -1.5000 0.0000 C 0 0 1 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 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 1.8270 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 24 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 31 2 0 0 0 0 21 2 1 1 0 0 0 21 22 1 0 0 0 0 22 29 1 1 0 0 0 23 24 1 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 32 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.35
Volume:	500.245
LogP:	6.99
LogD:	5.476
LogS:	-6.274
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	4.91
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.913
MDCK Permeability:	2.017481529037468e-05
Pgp-inhibitor:	0.893
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	97.23865509033203%
Volume Distribution (VD):	1.325
Pgp-substrate:	1.4932132959365845%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.377
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.462
CYP2C9-substrate:	0.203
CYP2D6-inhibitor:	0.44
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	5.165
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.973
Carcinogencity:	0.212
Eye Corrosion:	0.861
Eye Irritation:	0.366
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: NPC475772

Natural Product ID:	NPC475772
*Common Name:**	5 Alpha-Lanosta-7,9(11),24-Triene-3Beta-Hydroxy-26-Al
IUPAC Name:	(Z,6R)-6-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enal
Synonyms:
Standard InCHIKey:	RMOSHOXMAZYZOK-GJCSLOPBSA-N
Standard InCHI:	InChI=1S/C30H46O2/c1-20(19-31)9-8-10-21(2)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,11,14,19,21-22,25-26,32H,8,10,12-13,15-18H2,1-7H3/b20-9-/t21-,22-,25+,26+,28-,29-,30+/m1/s1
SMILES:	CC(CCC=C(C)C=O)C1CCC2(C1(CC=C3C2=CCC4C3(CCC(C4(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515080
PubChem CID:	44559674
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
NPO33360	ganoderma concinna	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908995]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	15.0	%	PMID[487486]

☑ 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 NPC475772 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	156
0.1-0.2	997
0.2-0.3	5219
0.3-0.4	15692
0.4-0.5	8714
0.5-0.6	6894
0.6-0.7	3864
0.7-0.8	1025
0.8-0.85	96
0.85-0.9	37
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9186	High Similarity	NPC191684
0.908	High Similarity	NPC212948
0.9059	High Similarity	NPC89747
0.8977	High Similarity	NPC214697
0.8941	High Similarity	NPC94755
0.8889	High Similarity	NPC186191
0.8889	High Similarity	NPC205455
0.8765	High Similarity	NPC214570
0.8764	High Similarity	NPC250575
0.875	High Similarity	NPC183283
0.8736	High Similarity	NPC471722
0.8721	High Similarity	NPC72133
0.8706	High Similarity	NPC472265
0.8706	High Similarity	NPC33913
0.869	High Similarity	NPC202389
0.869	High Similarity	NPC201852
0.8659	High Similarity	NPC275910
0.8659	High Similarity	NPC318136
0.8642	High Similarity	NPC46160
0.8642	High Similarity	NPC202642
0.8642	High Similarity	NPC73875
0.8636	High Similarity	NPC472240
0.8636	High Similarity	NPC84271
0.8636	High Similarity	NPC262858
0.8636	High Similarity	NPC86319
0.8636	High Similarity	NPC275740
0.8636	High Similarity	NPC102414
0.8636	High Similarity	NPC77168
0.8587	High Similarity	NPC141401
0.8571	High Similarity	NPC6707
0.8556	High Similarity	NPC134826
0.8537	High Similarity	NPC470428
0.8523	High Similarity	NPC143767
0.8523	High Similarity	NPC131470
0.8523	High Similarity	NPC471724
0.8519	High Similarity	NPC118508
0.8519	High Similarity	NPC121744
0.8519	High Similarity	NPC322353
0.8488	Intermediate Similarity	NPC473246
0.8488	Intermediate Similarity	NPC231310
0.8478	Intermediate Similarity	NPC190713
0.8471	Intermediate Similarity	NPC20853
0.8444	Intermediate Similarity	NPC272746
0.8434	Intermediate Similarity	NPC476949
0.8427	Intermediate Similarity	NPC146554
0.8415	Intermediate Similarity	NPC189883
0.8415	Intermediate Similarity	NPC470362
0.8409	Intermediate Similarity	NPC233836
0.8409	Intermediate Similarity	NPC475740
0.8409	Intermediate Similarity	NPC187376
0.8409	Intermediate Similarity	NPC141292
0.8409	Intermediate Similarity	NPC159046
0.8409	Intermediate Similarity	NPC136548
0.8391	Intermediate Similarity	NPC22133
0.8391	Intermediate Similarity	NPC280203
0.8391	Intermediate Similarity	NPC470574
0.8352	Intermediate Similarity	NPC69454
0.8333	Intermediate Similarity	NPC470429
0.8333	Intermediate Similarity	NPC85173
0.8333	Intermediate Similarity	NPC126993
0.8333	Intermediate Similarity	NPC1319
0.8315	Intermediate Similarity	NPC206060
0.8315	Intermediate Similarity	NPC328539
0.8315	Intermediate Similarity	NPC292491
0.8315	Intermediate Similarity	NPC310752
0.8298	Intermediate Similarity	NPC103051
0.8298	Intermediate Similarity	NPC92275
0.8295	Intermediate Similarity	NPC31564
0.8295	Intermediate Similarity	NPC475022
0.8295	Intermediate Similarity	NPC145879
0.8295	Intermediate Similarity	NPC222613
0.8295	Intermediate Similarity	NPC118648
0.8295	Intermediate Similarity	NPC28252
0.8295	Intermediate Similarity	NPC55309
0.8295	Intermediate Similarity	NPC474732
0.8295	Intermediate Similarity	NPC474733
0.8295	Intermediate Similarity	NPC474778
0.8293	Intermediate Similarity	NPC257347
0.8293	Intermediate Similarity	NPC141071
0.8293	Intermediate Similarity	NPC471723
0.8276	Intermediate Similarity	NPC214043
0.8276	Intermediate Similarity	NPC238485
0.8276	Intermediate Similarity	NPC85774
0.8272	Intermediate Similarity	NPC201373
0.8261	Intermediate Similarity	NPC469406
0.8256	Intermediate Similarity	NPC87489
0.8242	Intermediate Similarity	NPC110923
0.8242	Intermediate Similarity	NPC74296
0.8242	Intermediate Similarity	NPC63748
0.8242	Intermediate Similarity	NPC233116
0.8235	Intermediate Similarity	NPC236112
0.8222	Intermediate Similarity	NPC119416
0.8222	Intermediate Similarity	NPC309603
0.8222	Intermediate Similarity	NPC473999
0.8222	Intermediate Similarity	NPC31985
0.8222	Intermediate Similarity	NPC1015
0.8214	Intermediate Similarity	NPC6978
0.8214	Intermediate Similarity	NPC244385
0.8214	Intermediate Similarity	NPC18603
0.8214	Intermediate Similarity	NPC167037
0.8214	Intermediate Similarity	NPC285761
0.8214	Intermediate Similarity	NPC76931
0.8214	Intermediate Similarity	NPC138621
0.8214	Intermediate Similarity	NPC307965
0.8202	Intermediate Similarity	NPC474684
0.8202	Intermediate Similarity	NPC58063
0.8202	Intermediate Similarity	NPC142361
0.8193	Intermediate Similarity	NPC107059
0.8193	Intermediate Similarity	NPC129165
0.8193	Intermediate Similarity	NPC300324
0.8193	Intermediate Similarity	NPC321381
0.8193	Intermediate Similarity	NPC237460
0.8193	Intermediate Similarity	NPC250621
0.8193	Intermediate Similarity	NPC321016
0.8193	Intermediate Similarity	NPC240604
0.8193	Intermediate Similarity	NPC134330
0.8191	Intermediate Similarity	NPC99726
0.8182	Intermediate Similarity	NPC109528
0.8172	Intermediate Similarity	NPC45324
0.8172	Intermediate Similarity	NPC162001
0.8172	Intermediate Similarity	NPC259286
0.8172	Intermediate Similarity	NPC222845
0.8171	Intermediate Similarity	NPC78527
0.8161	Intermediate Similarity	NPC470384
0.8152	Intermediate Similarity	NPC38232
0.8152	Intermediate Similarity	NPC475255
0.8152	Intermediate Similarity	NPC476304
0.814	Intermediate Similarity	NPC6663
0.814	Intermediate Similarity	NPC6434
0.814	Intermediate Similarity	NPC474531
0.8132	Intermediate Similarity	NPC48010
0.8118	Intermediate Similarity	NPC273410
0.8118	Intermediate Similarity	NPC209430
0.8118	Intermediate Similarity	NPC30986
0.8118	Intermediate Similarity	NPC80530
0.8111	Intermediate Similarity	NPC474925
0.8111	Intermediate Similarity	NPC242864
0.8111	Intermediate Similarity	NPC470542
0.8095	Intermediate Similarity	NPC198968
0.8095	Intermediate Similarity	NPC318495
0.8095	Intermediate Similarity	NPC155986
0.809	Intermediate Similarity	NPC98236
0.809	Intermediate Similarity	NPC89077
0.809	Intermediate Similarity	NPC474970
0.809	Intermediate Similarity	NPC269396
0.8085	Intermediate Similarity	NPC249954
0.8085	Intermediate Similarity	NPC78473
0.8085	Intermediate Similarity	NPC192428
0.8072	Intermediate Similarity	NPC162742
0.8072	Intermediate Similarity	NPC22105
0.8072	Intermediate Similarity	NPC304309
0.8072	Intermediate Similarity	NPC288035
0.8072	Intermediate Similarity	NPC136188
0.8072	Intermediate Similarity	NPC134847
0.8072	Intermediate Similarity	NPC285893
0.8072	Intermediate Similarity	NPC28657
0.8072	Intermediate Similarity	NPC471468
0.8072	Intermediate Similarity	NPC230301
0.8068	Intermediate Similarity	NPC221758
0.8068	Intermediate Similarity	NPC59453
0.8065	Intermediate Similarity	NPC119562
0.8065	Intermediate Similarity	NPC279410
0.8065	Intermediate Similarity	NPC299100
0.8065	Intermediate Similarity	NPC476186
0.8065	Intermediate Similarity	NPC111015
0.8065	Intermediate Similarity	NPC196485
0.8065	Intermediate Similarity	NPC166906
0.8065	Intermediate Similarity	NPC245972
0.8049	Intermediate Similarity	NPC474140
0.8046	Intermediate Similarity	NPC470049
0.8046	Intermediate Similarity	NPC30166
0.8043	Intermediate Similarity	NPC475806
0.8043	Intermediate Similarity	NPC168027
0.8043	Intermediate Similarity	NPC185936
0.8043	Intermediate Similarity	NPC19114
0.8043	Intermediate Similarity	NPC473998
0.8023	Intermediate Similarity	NPC102253
0.8023	Intermediate Similarity	NPC13554
0.8023	Intermediate Similarity	NPC322313
0.8023	Intermediate Similarity	NPC236237
0.8022	Intermediate Similarity	NPC474704
0.8022	Intermediate Similarity	NPC186688
0.8022	Intermediate Similarity	NPC268406
0.8022	Intermediate Similarity	NPC26959
0.8022	Intermediate Similarity	NPC257485
0.8022	Intermediate Similarity	NPC475921
0.8022	Intermediate Similarity	NPC472983
0.8	Intermediate Similarity	NPC72507
0.8	Intermediate Similarity	NPC477522
0.8	Intermediate Similarity	NPC87604
0.8	Intermediate Similarity	NPC85346
0.8	Intermediate Similarity	NPC473943
0.8	Intermediate Similarity	NPC302041
0.8	Intermediate Similarity	NPC93778
0.8	Intermediate Similarity	NPC271967
0.8	Intermediate Similarity	NPC108078
0.8	Intermediate Similarity	NPC474216
0.8	Intermediate Similarity	NPC65897
0.7979	Intermediate Similarity	NPC127063
0.7979	Intermediate Similarity	NPC317586

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 NPC475772 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1288
0.2-0.3	4306
0.3-0.4	2495
0.4-0.5	499
0.5-0.6	162
0.6-0.7	176
0.7-0.8	79
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8444	Intermediate Similarity	NPD6079	Approved
0.8427	Intermediate Similarity	NPD5328	Approved
0.8295	Intermediate Similarity	NPD3618	Phase 1
0.8295	Intermediate Similarity	NPD5279	Phase 3
0.8085	Intermediate Similarity	NPD4697	Phase 3
0.8072	Intermediate Similarity	NPD7339	Approved
0.8072	Intermediate Similarity	NPD6942	Approved
0.8068	Intermediate Similarity	NPD4786	Approved
0.8023	Intermediate Similarity	NPD7525	Registered
0.7957	Intermediate Similarity	NPD4202	Approved
0.7895	Intermediate Similarity	NPD5222	Approved
0.7895	Intermediate Similarity	NPD5221	Approved
0.7895	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7841	Intermediate Similarity	NPD3667	Approved
0.7812	Intermediate Similarity	NPD5173	Approved
0.7765	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6924	Approved
0.7738	Intermediate Similarity	NPD6926	Approved
0.7701	Intermediate Similarity	NPD4195	Approved
0.7692	Intermediate Similarity	NPD4694	Approved
0.7692	Intermediate Similarity	NPD5280	Approved
0.7653	Intermediate Similarity	NPD5285	Approved
0.7653	Intermediate Similarity	NPD5286	Approved
0.7653	Intermediate Similarity	NPD4696	Approved
0.7629	Intermediate Similarity	NPD4755	Approved
0.7576	Intermediate Similarity	NPD5223	Approved
0.7558	Intermediate Similarity	NPD6933	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD7152	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD7150	Approved
0.75	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD7151	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7475	Intermediate Similarity	NPD4700	Approved
0.7474	Intermediate Similarity	NPD7515	Phase 2
0.747	Intermediate Similarity	NPD6923	Approved
0.747	Intermediate Similarity	NPD6922	Approved
0.7447	Intermediate Similarity	NPD4753	Phase 2
0.7444	Intermediate Similarity	NPD4221	Approved
0.7444	Intermediate Similarity	NPD4223	Phase 3
0.7426	Intermediate Similarity	NPD5174	Approved
0.7426	Intermediate Similarity	NPD5175	Approved
0.7416	Intermediate Similarity	NPD4748	Discontinued
0.7391	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5329	Approved
0.7381	Intermediate Similarity	NPD7144	Approved
0.7381	Intermediate Similarity	NPD7143	Approved
0.7374	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD5290	Discontinued
0.7353	Intermediate Similarity	NPD5141	Approved
0.7326	Intermediate Similarity	NPD5733	Approved
0.7312	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7303	Intermediate Similarity	NPD6929	Approved
0.73	Intermediate Similarity	NPD7640	Approved
0.73	Intermediate Similarity	NPD7639	Approved
0.7294	Intermediate Similarity	NPD4243	Approved
0.7292	Intermediate Similarity	NPD5284	Approved
0.7292	Intermediate Similarity	NPD5281	Approved
0.7283	Intermediate Similarity	NPD4197	Approved
0.7282	Intermediate Similarity	NPD5739	Approved
0.7282	Intermediate Similarity	NPD6675	Approved
0.7282	Intermediate Similarity	NPD6402	Approved
0.7282	Intermediate Similarity	NPD7128	Approved
0.7255	Intermediate Similarity	NPD4754	Approved
0.7245	Intermediate Similarity	NPD5210	Approved
0.7245	Intermediate Similarity	NPD4629	Approved
0.7241	Intermediate Similarity	NPD8264	Approved
0.7222	Intermediate Similarity	NPD7509	Discontinued
0.7222	Intermediate Similarity	NPD6930	Phase 2
0.7222	Intermediate Similarity	NPD6931	Approved
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7212	Intermediate Similarity	NPD5697	Approved
0.7188	Intermediate Similarity	NPD4096	Approved
0.7174	Intermediate Similarity	NPD4788	Approved
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD5168	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7128	Intermediate Similarity	NPD7521	Approved
0.7128	Intermediate Similarity	NPD4693	Phase 3
0.7128	Intermediate Similarity	NPD4138	Approved
0.7128	Intermediate Similarity	NPD5205	Approved
0.7128	Intermediate Similarity	NPD4689	Approved
0.7128	Intermediate Similarity	NPD4690	Approved
0.7128	Intermediate Similarity	NPD4688	Approved
0.7128	Intermediate Similarity	NPD7334	Approved
0.7128	Intermediate Similarity	NPD6684	Approved
0.7128	Intermediate Similarity	NPD7146	Approved
0.7128	Intermediate Similarity	NPD6409	Approved
0.7128	Intermediate Similarity	NPD5330	Approved
0.7126	Intermediate Similarity	NPD4784	Approved
0.7126	Intermediate Similarity	NPD4785	Approved
0.7126	Intermediate Similarity	NPD4687	Approved
0.7115	Intermediate Similarity	NPD4768	Approved
0.7115	Intermediate Similarity	NPD4767	Approved
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.71	Intermediate Similarity	NPD6083	Phase 2
0.71	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD3668	Phase 3
0.7093	Intermediate Similarity	NPD5276	Approved
0.7079	Intermediate Similarity	NPD5776	Phase 2
0.7079	Intermediate Similarity	NPD6932	Approved
0.7079	Intermediate Similarity	NPD6925	Approved
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7075	Intermediate Similarity	NPD6373	Approved
0.7075	Intermediate Similarity	NPD6372	Approved
0.7071	Intermediate Similarity	NPD5695	Phase 3
0.7053	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5701	Approved
0.7041	Intermediate Similarity	NPD5133	Approved
0.7037	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD8297	Approved
0.7033	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4634	Approved
0.7009	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5249	Phase 3
0.7009	Intermediate Similarity	NPD5247	Approved
0.7009	Intermediate Similarity	NPD5135	Approved
0.7009	Intermediate Similarity	NPD5169	Approved
0.7009	Intermediate Similarity	NPD5251	Approved
0.7009	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD7145	Approved
0.7	Intermediate Similarity	NPD3617	Approved
0.6989	Remote Similarity	NPD6695	Phase 3
0.6979	Remote Similarity	NPD6672	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5737	Approved
0.6979	Remote Similarity	NPD4518	Approved
0.6979	Remote Similarity	NPD6903	Approved
0.6961	Remote Similarity	NPD6404	Discontinued
0.6944	Remote Similarity	NPD5216	Approved
0.6944	Remote Similarity	NPD5127	Approved
0.6944	Remote Similarity	NPD5215	Approved
0.6944	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5217	Approved
0.6939	Remote Similarity	NPD6050	Approved
0.6932	Remote Similarity	NPD4058	Approved
0.6931	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD6683	Phase 2
0.6915	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4190	Phase 3
0.6854	Remote Similarity	NPD5275	Approved
0.6848	Remote Similarity	NPD4695	Discontinued
0.6848	Remote Similarity	NPD7514	Phase 3
0.6847	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD1696	Phase 3
0.6842	Remote Similarity	NPD6893	Approved
0.6837	Remote Similarity	NPD5207	Approved
0.6837	Remote Similarity	NPD5692	Phase 3
0.6818	Remote Similarity	NPD4632	Approved
0.6813	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7115	Discovery
0.6782	Remote Similarity	NPD4747	Approved
0.6782	Remote Similarity	NPD4691	Approved
0.6774	Remote Similarity	NPD4139	Approved
0.6774	Remote Similarity	NPD4692	Approved
0.6774	Remote Similarity	NPD6902	Approved
0.6768	Remote Similarity	NPD6411	Approved
0.6768	Remote Similarity	NPD8034	Phase 2
0.6768	Remote Similarity	NPD8035	Phase 2
0.6768	Remote Similarity	NPD5694	Approved
0.6757	Remote Similarity	NPD5167	Approved
0.6735	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6335	Approved
0.6705	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7524	Approved
0.6701	Remote Similarity	NPD7750	Discontinued
0.6699	Remote Similarity	NPD5696	Approved
0.6699	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD7101	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