NPASS Compound

Structure

NPC470165 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 -1.0182 3.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2954 -0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3054 2.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3272 2.2213 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5139 -1.6235 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9745 2.7565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4227 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2914 -2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 5 1 0 0 0 0 4 14 2 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 1 1 1 0 0 0 13 15 1 0 0 0 0 15 18 2 0 0 0 0 16 18 1 0 0 0 0 16 20 1 6 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	2.22
LogD:	1.693
LogS:	-4.185
# Rotatable Bonds:	3
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	4.793
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	1.8497934433980845e-05
Pgp-inhibitor:	0.257
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.818
Plasma Protein Binding (PPB):	84.38372039794922%
Volume Distribution (VD):	1.169
Pgp-substrate:	6.215602874755859%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.463
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.356
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.539
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	6.256
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.917
Carcinogencity:	0.7
Eye Corrosion:	0.753
Eye Irritation:	0.688
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC470165

Natural Product ID:	NPC470165
*Common Name:**	Sarcodonin G
IUPAC Name:	(3aR,5aR,10aR)-1-[(2S)-1-hydroxypropan-2-yl]-3a,5a-dimethyl-6-oxo-3,4,5,7,10,10a-hexahydro-2H-cyclohepta[e]indene-8-carbaldehyde
Synonyms:	Sarcodonin G; Sarcodonins G
Standard InCHIKey:	QCQNVTLNEHGTQY-SFNSOECISA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13(11-21)15-6-7-19(2)8-9-20(3)16(18(15)19)5-4-14(12-22)10-17(20)23/h4,12-13,16,21H,5-11H2,1-3H3/t13-,16-,19-,20-/m1/s1
SMILES:	OC[C@H](C1=C2[C@H]3CC=C(CC(=O)[C@]3(C)CC[C@]2(CC1)C)C=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802072
PubChem CID:	11162884
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
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22401866]
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	24.9	%	PMID[537386]

☑ 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 NPC470165 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	166
0.1-0.2	1177
0.2-0.3	6270
0.3-0.4	15547
0.4-0.5	8597
0.5-0.6	6888
0.6-0.7	3475
0.7-0.8	566
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8313	Intermediate Similarity	NPC136150
0.8193	Intermediate Similarity	NPC472478
0.8193	Intermediate Similarity	NPC2482
0.8182	Intermediate Similarity	NPC119416
0.8171	Intermediate Similarity	NPC297996
0.8171	Intermediate Similarity	NPC475994
0.8148	Intermediate Similarity	NPC470525
0.8148	Intermediate Similarity	NPC215481
0.814	Intermediate Similarity	NPC469948
0.8118	Intermediate Similarity	NPC307258
0.8111	Intermediate Similarity	NPC250575
0.8095	Intermediate Similarity	NPC90055
0.8095	Intermediate Similarity	NPC121984
0.8095	Intermediate Similarity	NPC116797
0.809	Intermediate Similarity	NPC191684
0.8072	Intermediate Similarity	NPC229204
0.8072	Intermediate Similarity	NPC472490
0.8072	Intermediate Similarity	NPC261125
0.8072	Intermediate Similarity	NPC181195
0.8068	Intermediate Similarity	NPC474677
0.8046	Intermediate Similarity	NPC118648
0.8046	Intermediate Similarity	NPC194417
0.8046	Intermediate Similarity	NPC475022
0.8046	Intermediate Similarity	NPC474778
0.8046	Intermediate Similarity	NPC474733
0.8046	Intermediate Similarity	NPC222613
0.8046	Intermediate Similarity	NPC145879
0.8046	Intermediate Similarity	NPC474732
0.8046	Intermediate Similarity	NPC31564
0.8023	Intermediate Similarity	NPC329043
0.8023	Intermediate Similarity	NPC321187
0.8023	Intermediate Similarity	NPC473246
0.8023	Intermediate Similarity	NPC470812
0.8023	Intermediate Similarity	NPC214043
0.8023	Intermediate Similarity	NPC58841
0.8023	Intermediate Similarity	NPC85774
0.8023	Intermediate Similarity	NPC227064
0.8023	Intermediate Similarity	NPC161423
0.8023	Intermediate Similarity	NPC237712
0.8	Intermediate Similarity	NPC131872
0.8	Intermediate Similarity	NPC151519
0.7978	Intermediate Similarity	NPC184663
0.7976	Intermediate Similarity	NPC45495
0.7976	Intermediate Similarity	NPC306095
0.7955	Intermediate Similarity	NPC58063
0.7955	Intermediate Similarity	NPC93778
0.7955	Intermediate Similarity	NPC475740
0.7952	Intermediate Similarity	NPC59436
0.7952	Intermediate Similarity	NPC62336
0.7931	Intermediate Similarity	NPC179006
0.7931	Intermediate Similarity	NPC142649
0.7931	Intermediate Similarity	NPC474853
0.7927	Intermediate Similarity	NPC263582
0.7912	Intermediate Similarity	NPC134826
0.7895	Intermediate Similarity	NPC237190
0.7889	Intermediate Similarity	NPC126993
0.7889	Intermediate Similarity	NPC85173
0.7865	Intermediate Similarity	NPC471722
0.7865	Intermediate Similarity	NPC473229
0.7865	Intermediate Similarity	NPC206060
0.7857	Intermediate Similarity	NPC7232
0.7857	Intermediate Similarity	NPC152061
0.7841	Intermediate Similarity	NPC327115
0.7831	Intermediate Similarity	NPC197659
0.7816	Intermediate Similarity	NPC221758
0.7816	Intermediate Similarity	NPC59453
0.7816	Intermediate Similarity	NPC472265
0.7816	Intermediate Similarity	NPC473157
0.7805	Intermediate Similarity	NPC474011
0.7805	Intermediate Similarity	NPC114236
0.7791	Intermediate Similarity	NPC142683
0.7791	Intermediate Similarity	NPC103486
0.7778	Intermediate Similarity	NPC1015
0.7778	Intermediate Similarity	NPC31985
0.7778	Intermediate Similarity	NPC186688
0.7778	Intermediate Similarity	NPC268406
0.7778	Intermediate Similarity	NPC477973
0.7778	Intermediate Similarity	NPC472983
0.7778	Intermediate Similarity	NPC26959
0.7765	Intermediate Similarity	NPC108955
0.7753	Intermediate Similarity	NPC136548
0.7753	Intermediate Similarity	NPC141292
0.7738	Intermediate Similarity	NPC80088
0.7738	Intermediate Similarity	NPC19443
0.7738	Intermediate Similarity	NPC253561
0.7738	Intermediate Similarity	NPC228911
0.7738	Intermediate Similarity	NPC189485
0.7727	Intermediate Similarity	NPC476426
0.7727	Intermediate Similarity	NPC70685
0.7727	Intermediate Similarity	NPC470574
0.7722	Intermediate Similarity	NPC155198
0.7717	Intermediate Similarity	NPC109305
0.7717	Intermediate Similarity	NPC474736
0.7711	Intermediate Similarity	NPC469796
0.7711	Intermediate Similarity	NPC469646
0.7711	Intermediate Similarity	NPC469793
0.7711	Intermediate Similarity	NPC242722
0.7711	Intermediate Similarity	NPC180886
0.7701	Intermediate Similarity	NPC476082
0.7701	Intermediate Similarity	NPC175410
0.7701	Intermediate Similarity	NPC278648
0.7692	Intermediate Similarity	NPC48010
0.7692	Intermediate Similarity	NPC183283
0.7692	Intermediate Similarity	NPC477711
0.7692	Intermediate Similarity	NPC129913
0.7684	Intermediate Similarity	NPC194196
0.7683	Intermediate Similarity	NPC78527
0.7674	Intermediate Similarity	NPC55869
0.7674	Intermediate Similarity	NPC119229
0.7674	Intermediate Similarity	NPC477372
0.7667	Intermediate Similarity	NPC477710
0.7667	Intermediate Similarity	NPC328539
0.7667	Intermediate Similarity	NPC292491
0.7667	Intermediate Similarity	NPC310752
0.766	Intermediate Similarity	NPC192428
0.766	Intermediate Similarity	NPC117133
0.766	Intermediate Similarity	NPC471039
0.7654	Intermediate Similarity	NPC474562
0.7647	Intermediate Similarity	NPC470429
0.7647	Intermediate Similarity	NPC308038
0.764	Intermediate Similarity	NPC72133
0.764	Intermediate Similarity	NPC6247
0.764	Intermediate Similarity	NPC472974
0.764	Intermediate Similarity	NPC51014
0.764	Intermediate Similarity	NPC94666
0.764	Intermediate Similarity	NPC20688
0.764	Intermediate Similarity	NPC94755
0.7634	Intermediate Similarity	NPC473162
0.7634	Intermediate Similarity	NPC471040
0.7619	Intermediate Similarity	NPC470428
0.7619	Intermediate Similarity	NPC106078
0.7619	Intermediate Similarity	NPC325946
0.7619	Intermediate Similarity	NPC276769
0.7614	Intermediate Similarity	NPC476412
0.7614	Intermediate Similarity	NPC82902
0.7614	Intermediate Similarity	NPC33913
0.7609	Intermediate Similarity	NPC230064
0.7609	Intermediate Similarity	NPC99380
0.7609	Intermediate Similarity	NPC272746
0.7609	Intermediate Similarity	NPC476187
0.7604	Intermediate Similarity	NPC112167
0.7595	Intermediate Similarity	NPC290350
0.7595	Intermediate Similarity	NPC4370
0.759	Intermediate Similarity	NPC472256
0.7586	Intermediate Similarity	NPC470813
0.7586	Intermediate Similarity	NPC310989
0.7586	Intermediate Similarity	NPC193347
0.7586	Intermediate Similarity	NPC320514
0.7582	Intermediate Similarity	NPC123912
0.7582	Intermediate Similarity	NPC477943
0.7582	Intermediate Similarity	NPC275740
0.7582	Intermediate Similarity	NPC5509
0.7582	Intermediate Similarity	NPC473999
0.7582	Intermediate Similarity	NPC86319
0.7582	Intermediate Similarity	NPC309603
0.7582	Intermediate Similarity	NPC326627
0.7582	Intermediate Similarity	NPC310010
0.7564	Intermediate Similarity	NPC474329
0.7564	Intermediate Similarity	NPC474304
0.7558	Intermediate Similarity	NPC472301
0.7558	Intermediate Similarity	NPC172013
0.7558	Intermediate Similarity	NPC471514
0.7558	Intermediate Similarity	NPC476809
0.7556	Intermediate Similarity	NPC470523
0.7553	Intermediate Similarity	NPC139459
0.7553	Intermediate Similarity	NPC473170
0.7529	Intermediate Similarity	NPC82635
0.7529	Intermediate Similarity	NPC275494
0.7529	Intermediate Similarity	NPC471409
0.7529	Intermediate Similarity	NPC178852
0.7529	Intermediate Similarity	NPC74410
0.7529	Intermediate Similarity	NPC476949
0.7529	Intermediate Similarity	NPC172066
0.7528	Intermediate Similarity	NPC79573
0.7528	Intermediate Similarity	NPC132228
0.7528	Intermediate Similarity	NPC471224
0.7528	Intermediate Similarity	NPC6185
0.7528	Intermediate Similarity	NPC474218
0.7528	Intermediate Similarity	NPC241512
0.7528	Intermediate Similarity	NPC474083
0.7528	Intermediate Similarity	NPC263997
0.7528	Intermediate Similarity	NPC8518
0.7528	Intermediate Similarity	NPC202868
0.7528	Intermediate Similarity	NPC29447
0.7527	Intermediate Similarity	NPC474807
0.7527	Intermediate Similarity	NPC12722
0.75	Intermediate Similarity	NPC168188
0.75	Intermediate Similarity	NPC470015
0.75	Intermediate Similarity	NPC472476
0.75	Intermediate Similarity	NPC474748
0.75	Intermediate Similarity	NPC64600
0.75	Intermediate Similarity	NPC8091
0.75	Intermediate Similarity	NPC215893
0.7474	Intermediate Similarity	NPC469545
0.7474	Intermediate Similarity	NPC5532
0.7474	Intermediate Similarity	NPC61369
0.7473	Intermediate Similarity	NPC471724
0.7473	Intermediate Similarity	NPC472483
0.7473	Intermediate Similarity	NPC131470
0.7473	Intermediate Similarity	NPC472802

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 NPC470165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1690
0.2-0.3	4126
0.3-0.4	2285
0.4-0.5	486
0.5-0.6	217
0.6-0.7	178
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD3665	Phase 1
0.8023	Intermediate Similarity	NPD3666	Approved
0.8023	Intermediate Similarity	NPD3133	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7841	Intermediate Similarity	NPD3618	Phase 1
0.7816	Intermediate Similarity	NPD4786	Approved
0.766	Intermediate Similarity	NPD4697	Phase 3
0.764	Intermediate Similarity	NPD5279	Phase 3
0.7609	Intermediate Similarity	NPD6079	Approved
0.7586	Intermediate Similarity	NPD4221	Approved
0.7586	Intermediate Similarity	NPD4223	Phase 3
0.7582	Intermediate Similarity	NPD4753	Phase 2
0.7582	Intermediate Similarity	NPD5328	Approved
0.7558	Intermediate Similarity	NPD4695	Discontinued
0.7444	Intermediate Similarity	NPD5690	Phase 2
0.7416	Intermediate Similarity	NPD4197	Approved
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD5329	Approved
0.7326	Intermediate Similarity	NPD3617	Approved
0.7317	Intermediate Similarity	NPD4691	Approved
0.7303	Intermediate Similarity	NPD4788	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7253	Intermediate Similarity	NPD4689	Approved
0.7253	Intermediate Similarity	NPD4138	Approved
0.7253	Intermediate Similarity	NPD4688	Approved
0.7253	Intermediate Similarity	NPD4519	Discontinued
0.7253	Intermediate Similarity	NPD4693	Phase 3
0.7253	Intermediate Similarity	NPD5205	Approved
0.7253	Intermediate Similarity	NPD4694	Approved
0.7253	Intermediate Similarity	NPD4623	Approved
0.7253	Intermediate Similarity	NPD4690	Approved
0.7253	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5280	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7216	Intermediate Similarity	NPD5173	Approved
0.7195	Intermediate Similarity	NPD4137	Phase 3
0.7158	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD1696	Phase 3
0.7108	Intermediate Similarity	NPD4747	Approved
0.7071	Intermediate Similarity	NPD5286	Approved
0.7071	Intermediate Similarity	NPD4696	Approved
0.7071	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD6409	Approved
0.7065	Intermediate Similarity	NPD6684	Approved
0.7065	Intermediate Similarity	NPD5330	Approved
0.7065	Intermediate Similarity	NPD7146	Approved
0.7065	Intermediate Similarity	NPD7521	Approved
0.7065	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD4058	Approved
0.7053	Intermediate Similarity	NPD7515	Phase 2
0.7045	Intermediate Similarity	NPD4195	Approved
0.7041	Intermediate Similarity	NPD4755	Approved
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD5223	Approved
0.6931	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD5226	Approved
0.6931	Remote Similarity	NPD5211	Phase 2
0.6931	Remote Similarity	NPD5225	Approved
0.6931	Remote Similarity	NPD4633	Approved
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6903	Approved
0.6915	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6672	Approved
0.69	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5175	Approved
0.6863	Remote Similarity	NPD5174	Approved
0.686	Remote Similarity	NPD4687	Approved
0.686	Remote Similarity	NPD5733	Approved
0.6829	Remote Similarity	NPD7331	Phase 2
0.6824	Remote Similarity	NPD5276	Approved
0.6813	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5696	Approved
0.6796	Remote Similarity	NPD5141	Approved
0.6782	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD5363	Approved
0.6771	Remote Similarity	NPD4096	Approved
0.6771	Remote Similarity	NPD5785	Approved
0.6742	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4518	Approved
0.6735	Remote Similarity	NPD7748	Approved
0.6707	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4139	Approved
0.6703	Remote Similarity	NPD4692	Approved
0.67	Remote Similarity	NPD7902	Approved
0.6699	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6926	Approved
0.6633	Remote Similarity	NPD5133	Approved
0.6604	Remote Similarity	NPD4729	Approved
0.6604	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD6899	Approved
0.6604	Remote Similarity	NPD5168	Approved
0.6604	Remote Similarity	NPD6881	Approved
0.6604	Remote Similarity	NPD4730	Approved
0.6604	Remote Similarity	NPD5128	Approved
0.6596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6922	Approved
0.6588	Remote Similarity	NPD6923	Approved
0.6574	Remote Similarity	NPD6650	Approved
0.6574	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD4767	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD4768	Approved
0.6566	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD5208	Approved
0.6559	Remote Similarity	NPD5362	Discontinued
0.6542	Remote Similarity	NPD6012	Approved
0.6542	Remote Similarity	NPD6013	Approved
0.6542	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD6373	Approved
0.6542	Remote Similarity	NPD6014	Approved
0.6522	Remote Similarity	NPD5369	Approved
0.6517	Remote Similarity	NPD6933	Approved
0.6512	Remote Similarity	NPD7143	Approved
0.6512	Remote Similarity	NPD7144	Approved
0.6509	Remote Similarity	NPD6412	Phase 2
0.6509	Remote Similarity	NPD5701	Approved
0.6506	Remote Similarity	NPD7341	Phase 2
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6080	Approved
0.6495	Remote Similarity	NPD6904	Approved
0.6481	Remote Similarity	NPD5250	Approved
0.6481	Remote Similarity	NPD7102	Approved
0.6481	Remote Similarity	NPD5248	Approved
0.6481	Remote Similarity	NPD5135	Approved
0.6481	Remote Similarity	NPD5251	Approved
0.6481	Remote Similarity	NPD5249	Phase 3
0.6481	Remote Similarity	NPD4634	Approved
0.6481	Remote Similarity	NPD7290	Approved
0.6481	Remote Similarity	NPD6883	Approved
0.6481	Remote Similarity	NPD5169	Approved
0.6481	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5247	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.6463	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3573	Approved
0.6452	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD4270	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD5091	Approved
0.6437	Remote Similarity	NPD7152	Approved
0.6437	Remote Similarity	NPD7150	Approved
0.6437	Remote Similarity	NPD7151	Approved
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD5692	Phase 3
0.6422	Remote Similarity	NPD5127	Approved
0.6422	Remote Similarity	NPD5217	Approved
0.6422	Remote Similarity	NPD6617	Approved
0.6422	Remote Similarity	NPD5216	Approved
0.6422	Remote Similarity	NPD8130	Phase 1
0.6422	Remote Similarity	NPD6869	Approved
0.6422	Remote Similarity	NPD6847	Approved
0.6422	Remote Similarity	NPD5215	Approved
0.6421	Remote Similarity	NPD1694	Approved
0.6413	Remote Similarity	NPD7525	Registered
0.6413	Remote Similarity	NPD5368	Approved
0.6413	Remote Similarity	NPD7509	Discontinued
0.6408	Remote Similarity	NPD7640	Approved
0.6408	Remote Similarity	NPD7639	Approved
0.64	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7900	Approved
0.6395	Remote Similarity	NPD3698	Phase 2
0.6395	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7154	Phase 3
0.6383	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD287	Approved
0.6374	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6364	Remote Similarity	NPD5693	Phase 1
0.6354	Remote Similarity	NPD6098	Approved
0.6354	Remote Similarity	NPD5786	Approved
0.6337	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4245	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.6322	Remote Similarity	NPD4244	Approved
0.6311	Remote Similarity	NPD5290	Discontinued
0.6311	Remote Similarity	NPD4225	Approved
0.6306	Remote Similarity	NPD4632	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