NPASS Compound

Structure

CID6663 OpenBabel06191715332D 23 25 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 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 -0.8660 1.5000 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 -0.0000 1.0000 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 0.0000 -2.0000 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 1.7321 0.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 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 -0.5000 0.0000 C 0 0 0 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 6 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 19 20 1 0 0 0 0 19 21 1 1 0 0 0 21 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.22
Volume:	353.137
LogP:	5.036
LogD:	4.129
LogS:	-4.943
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.789
Synthetic Accessibility Score:	3.928
Fsp3:	0.667
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:	-5.012
MDCK Permeability:	1.8282771634403616e-05
Pgp-inhibitor:	0.588
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	96.76740264892578%
Volume Distribution (VD):	3.04
Pgp-substrate:	2.8222804069519043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.127
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.531
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.395
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.526
CYP3A4-inhibitor:	0.457
CYP3A4-substrate:	0.658

ADMET: Excretion

Clearance (CL):	11.879
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.296
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.821
Maximum Recommended Daily Dose:	0.582
Skin Sensitization:	0.743
Carcinogencity:	0.032
Eye Corrosion:	0.006
Eye Irritation:	0.849
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC6663

Natural Product ID:	NPC6663
*Common Name:**	Taxodone
IUPAC Name:	(4bS,8aS,9S)-9-hydroxy-4,4b,8,8-tetramethyl-2-propan-2-yl-6,7,8a,9-tetrahydro-5H-phenanthren-3-one
Synonyms:	taxodone
Standard InCHIKey:	VQMBKPLOQBBIJU-NBHGPNQESA-N
Standard InCHI:	InChI=1S/C21H30O2/c1-12(2)15-10-14-11-16(22)19-20(4,5)8-7-9-21(19,6)17(14)13(3)18(15)23/h10-12,16,19,22H,7-9H2,1-6H3/t16-,19-,21+/m0/s1
SMILES:	O[C@H]1C=C2C=C(C(C)C)C(=O)C(=C2[C@@]2([C@@H]1C(C)(C)CCC2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497082
PubChem CID:	44592813
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17869103]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905523]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	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	7
Others	14

Activity Type	# Activity
Cell Line	21

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	57.0	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	54.3	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	47.0	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	22.0	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	20.0	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	3.5	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	13.0	%	PMID[558794]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9600.0	nM	PMID[558794]
NPT926	Cell Line	SK-MEL-1	Homo sapiens	IC50	=	7200.0	nM	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	FC	=	4.6	n.a.	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2700.0	nM	PMID[558794]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	2600.0	nM	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	FC	=	2.1	n.a.	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1800.0	nM	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	FC	=	1.5	n.a.	PMID[558794]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	1500.0	nM	PMID[558794]
NPT793	Cell Line	MOLT-3	Homo sapiens	IC50	=	1400.0	nM	PMID[558794]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	80.0	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	20.3	%	PMID[558794]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	36.0	%	PMID[558794]

☑ 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 NPC6663 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	162
0.1-0.2	912
0.2-0.3	4677
0.3-0.4	13366
0.4-0.5	11678
0.5-0.6	7055
0.6-0.7	3715
0.7-0.8	1053
0.8-0.85	70
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.878	High Similarity	NPC476426
0.8675	High Similarity	NPC472974
0.8608	High Similarity	NPC189485
0.8608	High Similarity	NPC475994
0.859	High Similarity	NPC250621
0.8553	High Similarity	NPC95863
0.8519	High Similarity	NPC116797
0.8519	High Similarity	NPC121984
0.85	High Similarity	NPC308038
0.85	High Similarity	NPC170394
0.8481	Intermediate Similarity	NPC203403
0.8452	Intermediate Similarity	NPC194417
0.8434	Intermediate Similarity	NPC476412
0.8391	Intermediate Similarity	NPC212948
0.8375	Intermediate Similarity	NPC62336
0.8354	Intermediate Similarity	NPC263582
0.8353	Intermediate Similarity	NPC287079
0.8353	Intermediate Similarity	NPC136548
0.8333	Intermediate Similarity	NPC109528
0.8333	Intermediate Similarity	NPC474083
0.8295	Intermediate Similarity	NPC214697
0.8276	Intermediate Similarity	NPC69622
0.8272	Intermediate Similarity	NPC19900
0.8272	Intermediate Similarity	NPC472490
0.8256	Intermediate Similarity	NPC72397
0.825	Intermediate Similarity	NPC74995
0.8242	Intermediate Similarity	NPC235464
0.8242	Intermediate Similarity	NPC166745
0.8235	Intermediate Similarity	NPC472986
0.8235	Intermediate Similarity	NPC472985
0.8214	Intermediate Similarity	NPC473246
0.8214	Intermediate Similarity	NPC472265
0.8205	Intermediate Similarity	NPC186042
0.8202	Intermediate Similarity	NPC474882
0.8193	Intermediate Similarity	NPC224455
0.8193	Intermediate Similarity	NPC38796
0.8193	Intermediate Similarity	NPC93590
0.8193	Intermediate Similarity	NPC103486
0.8193	Intermediate Similarity	NPC158411
0.8182	Intermediate Similarity	NPC34834
0.8171	Intermediate Similarity	NPC471514
0.8171	Intermediate Similarity	NPC472478
0.8171	Intermediate Similarity	NPC172013
0.8171	Intermediate Similarity	NPC271104
0.8171	Intermediate Similarity	NPC2482
0.8161	Intermediate Similarity	NPC472983
0.8161	Intermediate Similarity	NPC473999
0.8161	Intermediate Similarity	NPC472973
0.8161	Intermediate Similarity	NPC210216
0.8161	Intermediate Similarity	NPC309603
0.8158	Intermediate Similarity	NPC117804
0.814	Intermediate Similarity	NPC475772
0.8125	Intermediate Similarity	NPC470525
0.8118	Intermediate Similarity	NPC15807
0.8118	Intermediate Similarity	NPC32037
0.8118	Intermediate Similarity	NPC274724
0.8118	Intermediate Similarity	NPC471224
0.8095	Intermediate Similarity	NPC49019
0.8095	Intermediate Similarity	NPC57370
0.809	Intermediate Similarity	NPC474736
0.809	Intermediate Similarity	NPC250575
0.809	Intermediate Similarity	NPC109305
0.809	Intermediate Similarity	NPC472942
0.809	Intermediate Similarity	NPC134826
0.809	Intermediate Similarity	NPC69454
0.809	Intermediate Similarity	NPC472930
0.8072	Intermediate Similarity	NPC470298
0.8072	Intermediate Similarity	NPC4166
0.8072	Intermediate Similarity	NPC6434
0.8068	Intermediate Similarity	NPC48010
0.8052	Intermediate Similarity	NPC471560
0.8049	Intermediate Similarity	NPC27817
0.8049	Intermediate Similarity	NPC281138
0.8049	Intermediate Similarity	NPC474113
0.8049	Intermediate Similarity	NPC152061
0.8043	Intermediate Similarity	NPC471717
0.8043	Intermediate Similarity	NPC103051
0.8025	Intermediate Similarity	NPC197659
0.8023	Intermediate Similarity	NPC470955
0.8023	Intermediate Similarity	NPC475022
0.8023	Intermediate Similarity	NPC222613
0.8023	Intermediate Similarity	NPC118648
0.8022	Intermediate Similarity	NPC190713
0.8022	Intermediate Similarity	NPC117133
0.8022	Intermediate Similarity	NPC472941
0.8022	Intermediate Similarity	NPC456
0.8	Intermediate Similarity	NPC85774
0.8	Intermediate Similarity	NPC299100
0.8	Intermediate Similarity	NPC227132
0.8	Intermediate Similarity	NPC227064
0.8	Intermediate Similarity	NPC33913
0.8	Intermediate Similarity	NPC58841
0.8	Intermediate Similarity	NPC321187
0.8	Intermediate Similarity	NPC53385
0.8	Intermediate Similarity	NPC214043
0.8	Intermediate Similarity	NPC302360
0.8	Intermediate Similarity	NPC473162
0.8	Intermediate Similarity	NPC329043
0.8	Intermediate Similarity	NPC161423
0.7978	Intermediate Similarity	NPC19114
0.7978	Intermediate Similarity	NPC475806
0.7978	Intermediate Similarity	NPC233116
0.7978	Intermediate Similarity	NPC472978
0.7978	Intermediate Similarity	NPC63748
0.7978	Intermediate Similarity	NPC473998
0.7976	Intermediate Similarity	NPC202389
0.7976	Intermediate Similarity	NPC311092
0.7975	Intermediate Similarity	NPC130665
0.7955	Intermediate Similarity	NPC262858
0.7955	Intermediate Similarity	NPC123912
0.7955	Intermediate Similarity	NPC472240
0.7955	Intermediate Similarity	NPC146554
0.7952	Intermediate Similarity	NPC157895
0.7952	Intermediate Similarity	NPC104120
0.7952	Intermediate Similarity	NPC108955
0.7952	Intermediate Similarity	NPC148685
0.7935	Intermediate Similarity	NPC141401
0.7931	Intermediate Similarity	NPC220930
0.7931	Intermediate Similarity	NPC272039
0.7927	Intermediate Similarity	NPC275494
0.7927	Intermediate Similarity	NPC297996
0.7927	Intermediate Similarity	NPC471409
0.7922	Intermediate Similarity	NPC216460
0.7912	Intermediate Similarity	NPC259286
0.7912	Intermediate Similarity	NPC472932
0.7912	Intermediate Similarity	NPC180950
0.7907	Intermediate Similarity	NPC179006
0.7907	Intermediate Similarity	NPC474853
0.7882	Intermediate Similarity	NPC41539
0.7882	Intermediate Similarity	NPC309309
0.7882	Intermediate Similarity	NPC470384
0.7882	Intermediate Similarity	NPC297398
0.7882	Intermediate Similarity	NPC105173
0.7882	Intermediate Similarity	NPC291999
0.7875	Intermediate Similarity	NPC215050
0.7872	Intermediate Similarity	NPC472637
0.7872	Intermediate Similarity	NPC99411
0.7865	Intermediate Similarity	NPC191684
0.7865	Intermediate Similarity	NPC129913
0.7857	Intermediate Similarity	NPC55869
0.7857	Intermediate Similarity	NPC225515
0.7849	Intermediate Similarity	NPC197386
0.7849	Intermediate Similarity	NPC478056
0.7841	Intermediate Similarity	NPC471722
0.7841	Intermediate Similarity	NPC229612
0.7841	Intermediate Similarity	NPC471791
0.7841	Intermediate Similarity	NPC24816
0.7841	Intermediate Similarity	NPC7280
0.7841	Intermediate Similarity	NPC471793
0.7826	Intermediate Similarity	NPC249954
0.7826	Intermediate Similarity	NPC301534
0.7826	Intermediate Similarity	NPC250757
0.7821	Intermediate Similarity	NPC474248
0.7816	Intermediate Similarity	NPC474732
0.7816	Intermediate Similarity	NPC474733
0.7816	Intermediate Similarity	NPC82979
0.7816	Intermediate Similarity	NPC473168
0.7816	Intermediate Similarity	NPC31564
0.7816	Intermediate Similarity	NPC72133
0.7816	Intermediate Similarity	NPC94666
0.7816	Intermediate Similarity	NPC145879
0.7816	Intermediate Similarity	NPC327115
0.7816	Intermediate Similarity	NPC89077
0.7816	Intermediate Similarity	NPC469994
0.7816	Intermediate Similarity	NPC322159
0.7816	Intermediate Similarity	NPC474778
0.7805	Intermediate Similarity	NPC97377
0.7805	Intermediate Similarity	NPC91594
0.7805	Intermediate Similarity	NPC470428
0.7805	Intermediate Similarity	NPC257666
0.7805	Intermediate Similarity	NPC325946
0.7805	Intermediate Similarity	NPC266193
0.7802	Intermediate Similarity	NPC8993
0.7802	Intermediate Similarity	NPC474690
0.7802	Intermediate Similarity	NPC469406
0.7802	Intermediate Similarity	NPC472976
0.7802	Intermediate Similarity	NPC472977
0.7792	Intermediate Similarity	NPC114651
0.7791	Intermediate Similarity	NPC238485
0.7791	Intermediate Similarity	NPC231310
0.7791	Intermediate Similarity	NPC87552
0.7791	Intermediate Similarity	NPC237712
0.7778	Intermediate Similarity	NPC313179
0.7778	Intermediate Similarity	NPC171148
0.7778	Intermediate Similarity	NPC474885
0.7778	Intermediate Similarity	NPC472975
0.7778	Intermediate Similarity	NPC114236
0.7778	Intermediate Similarity	NPC69383
0.7778	Intermediate Similarity	NPC204341
0.7766	Intermediate Similarity	NPC287833
0.7765	Intermediate Similarity	NPC151519
0.7765	Intermediate Similarity	NPC92226
0.7753	Intermediate Similarity	NPC214387
0.7753	Intermediate Similarity	NPC118011
0.7753	Intermediate Similarity	NPC86319
0.7753	Intermediate Similarity	NPC119416
0.7753	Intermediate Similarity	NPC2983
0.7753	Intermediate Similarity	NPC314727
0.7753	Intermediate Similarity	NPC36668
0.7753	Intermediate Similarity	NPC275740

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 NPC6663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1221
0.2-0.3	3861
0.3-0.4	2708
0.4-0.5	760
0.5-0.6	225
0.6-0.7	202
0.7-0.8	21
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
0.8235	Intermediate Similarity	NPD5279	Phase 3
0.8	Intermediate Similarity	NPD3665	Phase 1
0.8	Intermediate Similarity	NPD3666	Approved
0.8	Intermediate Similarity	NPD3133	Approved
0.7816	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD8264	Approved
0.7765	Intermediate Similarity	NPD3667	Approved
0.7701	Intermediate Similarity	NPD1696	Phase 3
0.7614	Intermediate Similarity	NPD5280	Approved
0.7614	Intermediate Similarity	NPD4519	Discontinued
0.7614	Intermediate Similarity	NPD4623	Approved
0.7614	Intermediate Similarity	NPD4694	Approved
0.7586	Intermediate Similarity	NPD4786	Approved
0.7582	Intermediate Similarity	NPD6079	Approved
0.7556	Intermediate Similarity	NPD5328	Approved
0.7529	Intermediate Similarity	NPD4695	Discontinued
0.7416	Intermediate Similarity	NPD5690	Phase 2
0.7412	Intermediate Similarity	NPD4195	Approved
0.7391	Intermediate Similarity	NPD7515	Phase 2
0.7363	Intermediate Similarity	NPD4753	Phase 2
0.7356	Intermediate Similarity	NPD4223	Phase 3
0.7356	Intermediate Similarity	NPD4221	Approved
0.7326	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4202	Approved
0.7263	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5222	Approved
0.7263	Intermediate Similarity	NPD5221	Approved
0.7262	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5211	Phase 2
0.7229	Intermediate Similarity	NPD4687	Approved
0.7229	Intermediate Similarity	NPD5733	Approved
0.7229	Intermediate Similarity	NPD4058	Approved
0.7204	Intermediate Similarity	NPD5284	Approved
0.7204	Intermediate Similarity	NPD5281	Approved
0.7195	Intermediate Similarity	NPD5276	Approved
0.7191	Intermediate Similarity	NPD4197	Approved
0.7188	Intermediate Similarity	NPD5173	Approved
0.7174	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5210	Approved
0.7158	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD7339	Approved
0.7111	Intermediate Similarity	NPD5329	Approved
0.71	Intermediate Similarity	NPD5141	Approved
0.7097	Intermediate Similarity	NPD4096	Approved
0.7093	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3617	Approved
0.7083	Intermediate Similarity	NPD4697	Phase 3
0.7073	Intermediate Similarity	NPD4691	Approved
0.7053	Intermediate Similarity	NPD7748	Approved
0.7041	Intermediate Similarity	NPD7639	Approved
0.7041	Intermediate Similarity	NPD5286	Approved
0.7041	Intermediate Similarity	NPD4696	Approved
0.7041	Intermediate Similarity	NPD6404	Discontinued
0.7041	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD7640	Approved
0.7033	Intermediate Similarity	NPD6409	Approved
0.7033	Intermediate Similarity	NPD7146	Approved
0.7033	Intermediate Similarity	NPD6684	Approved
0.7033	Intermediate Similarity	NPD4693	Phase 3
0.7033	Intermediate Similarity	NPD5330	Approved
0.7033	Intermediate Similarity	NPD4689	Approved
0.7033	Intermediate Similarity	NPD4138	Approved
0.7033	Intermediate Similarity	NPD4690	Approved
0.7033	Intermediate Similarity	NPD7521	Approved
0.7033	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4688	Approved
0.7033	Intermediate Similarity	NPD5205	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD6929	Approved
0.7011	Intermediate Similarity	NPD7645	Phase 2
0.701	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD3668	Phase 3
0.6979	Remote Similarity	NPD5695	Phase 3
0.6977	Remote Similarity	NPD5776	Phase 2
0.6977	Remote Similarity	NPD6925	Approved
0.697	Remote Similarity	NPD5223	Approved
0.6957	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6922	Approved
0.6951	Remote Similarity	NPD6923	Approved
0.6951	Remote Similarity	NPD4137	Phase 3
0.6947	Remote Similarity	NPD5133	Approved
0.6939	Remote Similarity	NPD4225	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6932	Remote Similarity	NPD7332	Phase 2
0.6932	Remote Similarity	NPD6930	Phase 2
0.6932	Remote Similarity	NPD7514	Phase 3
0.6932	Remote Similarity	NPD6931	Approved
0.6923	Remote Similarity	NPD368	Approved
0.69	Remote Similarity	NPD5226	Approved
0.69	Remote Similarity	NPD5224	Approved
0.69	Remote Similarity	NPD4633	Approved
0.69	Remote Similarity	NPD5225	Approved
0.6897	Remote Similarity	NPD7145	Approved
0.6889	Remote Similarity	NPD4788	Approved
0.6882	Remote Similarity	NPD4518	Approved
0.6882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD4700	Approved
0.6867	Remote Similarity	NPD4747	Approved
0.6867	Remote Similarity	NPD7143	Approved
0.6867	Remote Similarity	NPD7144	Approved
0.686	Remote Similarity	NPD6933	Approved
0.6854	Remote Similarity	NPD6902	Approved
0.6842	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD6084	Phase 2
0.6837	Remote Similarity	NPD6083	Phase 2
0.6837	Remote Similarity	NPD7902	Approved
0.6832	Remote Similarity	NPD5174	Approved
0.6832	Remote Similarity	NPD5175	Approved
0.6786	Remote Similarity	NPD7152	Approved
0.6786	Remote Similarity	NPD7151	Approved
0.6786	Remote Similarity	NPD7150	Approved
0.6778	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD6399	Phase 3
0.6768	Remote Similarity	NPD5290	Discontinued
0.6742	Remote Similarity	NPD7525	Registered
0.6739	Remote Similarity	NPD1694	Approved
0.6737	Remote Similarity	NPD5692	Phase 3
0.6737	Remote Similarity	NPD5207	Approved
0.6711	Remote Similarity	NPD4219	Approved
0.6709	Remote Similarity	NPD4191	Approved
0.6709	Remote Similarity	NPD4194	Approved
0.6709	Remote Similarity	NPD4192	Approved
0.6709	Remote Similarity	NPD4193	Approved
0.6705	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6695	Phase 3
0.6702	Remote Similarity	NPD5737	Approved
0.6702	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD6898	Phase 1
0.6667	Remote Similarity	NPD4692	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.663	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5696	Approved
0.6596	Remote Similarity	NPD3573	Approved
0.6591	Remote Similarity	NPD6932	Approved
0.6588	Remote Similarity	NPD4243	Approved
0.6585	Remote Similarity	NPD7331	Phase 2
0.6579	Remote Similarity	NPD342	Phase 1
0.6571	Remote Similarity	NPD6011	Approved
0.6571	Remote Similarity	NPD5168	Approved
0.6571	Remote Similarity	NPD5128	Approved
0.6571	Remote Similarity	NPD4730	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD4729	Approved
0.6566	Remote Similarity	NPD7614	Phase 1
0.6562	Remote Similarity	NPD5785	Approved
0.6559	Remote Similarity	NPD6893	Approved
0.6559	Remote Similarity	NPD5363	Approved
0.6556	Remote Similarity	NPD4748	Discontinued
0.6556	Remote Similarity	NPD7509	Discontinued
0.6545	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD4768	Approved
0.6538	Remote Similarity	NPD4767	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6531	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.6509	Remote Similarity	NPD6013	Approved
0.6476	Remote Similarity	NPD6412	Phase 2
0.6476	Remote Similarity	NPD5701	Approved
0.6452	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6449	Remote Similarity	NPD5248	Approved
0.6449	Remote Similarity	NPD5251	Approved
0.6449	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4634	Approved
0.6449	Remote Similarity	NPD5247	Approved
0.6449	Remote Similarity	NPD5169	Approved
0.6449	Remote Similarity	NPD5135	Approved
0.6449	Remote Similarity	NPD5249	Phase 3
0.6449	Remote Similarity	NPD5250	Approved
0.6444	Remote Similarity	NPD6683	Phase 2
0.6437	Remote Similarity	NPD4785	Approved
0.6437	Remote Similarity	NPD4784	Approved
0.6429	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7524	Approved
0.6421	Remote Similarity	NPD7750	Discontinued
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6686	Approved
0.6413	Remote Similarity	NPD5209	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