NPASS Compound

Structure

CID2648 OpenBabel06191715322D 22 24 0 0 1 0 0 0 0 0999 V2000 -3.4051 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6015 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 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 -2.6980 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 0.8660 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 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 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 0.0000 -1.0000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 17 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 2 1 1 0 0 0 18 3 1 6 0 0 0 19 4 1 1 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.26
Volume:	343.751
LogP:	3.156
LogD:	2.733
LogS:	-3.504
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	4.691
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.782
MDCK Permeability:	1.5167231140367221e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.236

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	88.47125244140625%
Volume Distribution (VD):	0.898
Pgp-substrate:	11.561297416687012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	5.913
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.404
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.815
Carcinogencity:	0.146
Eye Corrosion:	0.553
Eye Irritation:	0.165
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC2648

Natural Product ID:	NPC2648
*Common Name:**	Akhdardiol
IUPAC Name:	(1S,4aS,4bR,7S,8aR,10aR)-7-ethenyl-1-(hydroxymethyl)-1,4a,7-trimethyl-2,3,4,4b,5,6,8,9,10,10a-decahydrophenanthren-8a-ol
Synonyms:	Akhdardiol
Standard InCHIKey:	RIQATFSOVFFVRX-HMGBVJPOSA-N
Standard InCHI:	InChI=1S/C20H34O2/c1-5-17(2)11-7-16-19(4)10-6-9-18(3,14-21)15(19)8-12-20(16,22)13-17/h5,15-16,21-22H,1,6-14H2,2-4H3/t15-,16+,17-,18+,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2[C@@](C1)(O)CC[C@@H]1[C@]2(C)CCC[C@]1(C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094092
PubChem CID:	13996017
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
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6891	Taiwanofungus salmoneus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8610	Porites rus	Species	Poritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[493708]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[493708]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[493708]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[493708]

☑ 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 NPC2648 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	190
0.1-0.2	2206
0.2-0.3	10569
0.3-0.4	15319
0.4-0.5	5717
0.5-0.6	5356
0.6-0.7	2478
0.7-0.8	721
0.8-0.85	125
0.85-0.9	13
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC210323
0.8732	High Similarity	NPC470749
0.8696	High Similarity	NPC167706
0.8676	High Similarity	NPC9942
0.8657	High Similarity	NPC117607
0.8657	High Similarity	NPC88454
0.8657	High Similarity	NPC101307
0.8636	High Similarity	NPC64123
0.8611	High Similarity	NPC470711
0.8611	High Similarity	NPC470758
0.8611	High Similarity	NPC169994
0.8611	High Similarity	NPC472746
0.8592	High Similarity	NPC3403
0.8592	High Similarity	NPC103822
0.8571	High Similarity	NPC182717
0.8571	High Similarity	NPC211009
0.8551	High Similarity	NPC45296
0.8529	High Similarity	NPC94192
0.8507	High Similarity	NPC476406
0.8493	Intermediate Similarity	NPC137587
0.8493	Intermediate Similarity	NPC148977
0.8493	Intermediate Similarity	NPC285761
0.8493	Intermediate Similarity	NPC11908
0.8485	Intermediate Similarity	NPC101128
0.8472	Intermediate Similarity	NPC106432
0.8472	Intermediate Similarity	NPC91573
0.8472	Intermediate Similarity	NPC63958
0.8451	Intermediate Similarity	NPC91858
0.8451	Intermediate Similarity	NPC477138
0.8451	Intermediate Similarity	NPC308440
0.8451	Intermediate Similarity	NPC162164
0.8451	Intermediate Similarity	NPC476366
0.8451	Intermediate Similarity	NPC100334
0.8451	Intermediate Similarity	NPC201048
0.8451	Intermediate Similarity	NPC243342
0.8451	Intermediate Similarity	NPC476736
0.8451	Intermediate Similarity	NPC472503
0.8429	Intermediate Similarity	NPC110799
0.8429	Intermediate Similarity	NPC111234
0.8429	Intermediate Similarity	NPC301226
0.8413	Intermediate Similarity	NPC135438
0.8382	Intermediate Similarity	NPC185874
0.8382	Intermediate Similarity	NPC253303
0.8382	Intermediate Similarity	NPC269077
0.8382	Intermediate Similarity	NPC139207
0.8378	Intermediate Similarity	NPC80530
0.8378	Intermediate Similarity	NPC291379
0.8378	Intermediate Similarity	NPC273410
0.8358	Intermediate Similarity	NPC258595
0.8356	Intermediate Similarity	NPC90979
0.8356	Intermediate Similarity	NPC157996
0.8356	Intermediate Similarity	NPC40394
0.8356	Intermediate Similarity	NPC472805
0.8356	Intermediate Similarity	NPC471798
0.8356	Intermediate Similarity	NPC34177
0.8356	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC291503
0.8333	Intermediate Similarity	NPC34700
0.8333	Intermediate Similarity	NPC185536
0.8333	Intermediate Similarity	NPC104387
0.8333	Intermediate Similarity	NPC138374
0.8333	Intermediate Similarity	NPC230704
0.8333	Intermediate Similarity	NPC240235
0.8333	Intermediate Similarity	NPC70982
0.8333	Intermediate Similarity	NPC178383
0.8333	Intermediate Similarity	NPC212879
0.8333	Intermediate Similarity	NPC144075
0.8333	Intermediate Similarity	NPC231256
0.831	Intermediate Similarity	NPC471799
0.8289	Intermediate Similarity	NPC218616
0.8289	Intermediate Similarity	NPC296701
0.8267	Intermediate Similarity	NPC102253
0.8267	Intermediate Similarity	NPC13554
0.8267	Intermediate Similarity	NPC322313
0.8267	Intermediate Similarity	NPC236237
0.8261	Intermediate Similarity	NPC244790
0.8243	Intermediate Similarity	NPC22955
0.8243	Intermediate Similarity	NPC301707
0.8243	Intermediate Similarity	NPC472342
0.8243	Intermediate Similarity	NPC72507
0.8243	Intermediate Similarity	NPC474989
0.8243	Intermediate Similarity	NPC472501
0.8243	Intermediate Similarity	NPC158662
0.8243	Intermediate Similarity	NPC99168
0.8243	Intermediate Similarity	NPC244385
0.8243	Intermediate Similarity	NPC230295
0.8243	Intermediate Similarity	NPC196753
0.8243	Intermediate Similarity	NPC138621
0.8243	Intermediate Similarity	NPC42853
0.8243	Intermediate Similarity	NPC6978
0.8243	Intermediate Similarity	NPC470396
0.8243	Intermediate Similarity	NPC253807
0.8243	Intermediate Similarity	NPC300499
0.8243	Intermediate Similarity	NPC98386
0.8243	Intermediate Similarity	NPC31828
0.8243	Intermediate Similarity	NPC167037
0.8219	Intermediate Similarity	NPC290598
0.8219	Intermediate Similarity	NPC122418
0.8219	Intermediate Similarity	NPC27765
0.8219	Intermediate Similarity	NPC104806
0.8219	Intermediate Similarity	NPC470766
0.8219	Intermediate Similarity	NPC278091
0.8219	Intermediate Similarity	NPC30590
0.8219	Intermediate Similarity	NPC265328
0.8219	Intermediate Similarity	NPC93662
0.8219	Intermediate Similarity	NPC265588
0.8219	Intermediate Similarity	NPC78067
0.8219	Intermediate Similarity	NPC14112
0.8219	Intermediate Similarity	NPC237460
0.8219	Intermediate Similarity	NPC86305
0.8219	Intermediate Similarity	NPC120098
0.8209	Intermediate Similarity	NPC144650
0.8194	Intermediate Similarity	NPC5046
0.8194	Intermediate Similarity	NPC49168
0.8194	Intermediate Similarity	NPC196358
0.8194	Intermediate Similarity	NPC145552
0.8194	Intermediate Similarity	NPC471797
0.8194	Intermediate Similarity	NPC62657
0.8194	Intermediate Similarity	NPC192638
0.8194	Intermediate Similarity	NPC254509
0.8194	Intermediate Similarity	NPC38426
0.8194	Intermediate Similarity	NPC25511
0.8182	Intermediate Similarity	NPC82623
0.8182	Intermediate Similarity	NPC470558
0.8182	Intermediate Similarity	NPC134481
0.8169	Intermediate Similarity	NPC242001
0.8143	Intermediate Similarity	NPC476431
0.8133	Intermediate Similarity	NPC49599
0.8133	Intermediate Similarity	NPC472463
0.8133	Intermediate Similarity	NPC49627
0.8133	Intermediate Similarity	NPC53744
0.8125	Intermediate Similarity	NPC236588
0.8116	Intermediate Similarity	NPC197805
0.8108	Intermediate Similarity	NPC331618
0.8108	Intermediate Similarity	NPC91594
0.8108	Intermediate Similarity	NPC202540
0.8108	Intermediate Similarity	NPC212241
0.8108	Intermediate Similarity	NPC260301
0.8108	Intermediate Similarity	NPC119355
0.8108	Intermediate Similarity	NPC257191
0.8108	Intermediate Similarity	NPC248830
0.8108	Intermediate Similarity	NPC307336
0.8108	Intermediate Similarity	NPC138502
0.8088	Intermediate Similarity	NPC476737
0.8088	Intermediate Similarity	NPC11555
0.8088	Intermediate Similarity	NPC208198
0.8088	Intermediate Similarity	NPC27243
0.8088	Intermediate Similarity	NPC282619
0.8088	Intermediate Similarity	NPC172613
0.8088	Intermediate Similarity	NPC60837
0.8088	Intermediate Similarity	NPC80463
0.8088	Intermediate Similarity	NPC260116
0.8088	Intermediate Similarity	NPC2728
0.8082	Intermediate Similarity	NPC32832
0.8082	Intermediate Similarity	NPC66566
0.8082	Intermediate Similarity	NPC200243
0.8082	Intermediate Similarity	NPC477923
0.8077	Intermediate Similarity	NPC474493
0.8056	Intermediate Similarity	NPC195489
0.8056	Intermediate Similarity	NPC68443
0.8028	Intermediate Similarity	NPC145498
0.8026	Intermediate Similarity	NPC295131
0.8	Intermediate Similarity	NPC245795
0.8	Intermediate Similarity	NPC477819
0.8	Intermediate Similarity	NPC302041
0.8	Intermediate Similarity	NPC276616
0.8	Intermediate Similarity	NPC65897
0.8	Intermediate Similarity	NPC477817
0.8	Intermediate Similarity	NPC85346
0.8	Intermediate Similarity	NPC472500
0.8	Intermediate Similarity	NPC474769
0.8	Intermediate Similarity	NPC32055
0.8	Intermediate Similarity	NPC312328
0.8	Intermediate Similarity	NPC102708
0.8	Intermediate Similarity	NPC472499
0.8	Intermediate Similarity	NPC189290
0.7975	Intermediate Similarity	NPC164424
0.7975	Intermediate Similarity	NPC477578
0.7973	Intermediate Similarity	NPC129165
0.7973	Intermediate Similarity	NPC38141
0.7973	Intermediate Similarity	NPC134330
0.7973	Intermediate Similarity	NPC106364
0.7973	Intermediate Similarity	NPC189883
0.7971	Intermediate Similarity	NPC42630
0.7971	Intermediate Similarity	NPC473929
0.7971	Intermediate Similarity	NPC286669
0.7971	Intermediate Similarity	NPC222366
0.7971	Intermediate Similarity	NPC476039
0.7949	Intermediate Similarity	NPC207013
0.7949	Intermediate Similarity	NPC477818
0.7949	Intermediate Similarity	NPC193870
0.7949	Intermediate Similarity	NPC82538
0.7949	Intermediate Similarity	NPC141941
0.7949	Intermediate Similarity	NPC237795
0.7941	Intermediate Similarity	NPC68656
0.7922	Intermediate Similarity	NPC249423
0.7922	Intermediate Similarity	NPC476646
0.7922	Intermediate Similarity	NPC242350
0.7922	Intermediate Similarity	NPC116202
0.7917	Intermediate Similarity	NPC164022

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 NPC2648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2644
0.2-0.3	4091
0.3-0.4	1607
0.4-0.5	309
0.5-0.6	206
0.6-0.7	115
0.7-0.8	7
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
0.8267	Intermediate Similarity	NPD7525	Registered
0.8133	Intermediate Similarity	NPD7645	Phase 2
0.7639	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6942	Approved
0.76	Intermediate Similarity	NPD7339	Approved
0.75	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4787	Phase 1
0.7237	Intermediate Similarity	NPD4784	Approved
0.7237	Intermediate Similarity	NPD6924	Approved
0.7237	Intermediate Similarity	NPD6926	Approved
0.7237	Intermediate Similarity	NPD4785	Approved
0.72	Intermediate Similarity	NPD4243	Approved
0.7073	Intermediate Similarity	NPD4788	Approved
0.7051	Intermediate Similarity	NPD6933	Approved
0.7024	Intermediate Similarity	NPD3618	Phase 1
0.7011	Intermediate Similarity	NPD6079	Approved
0.7011	Intermediate Similarity	NPD7515	Phase 2
0.6988	Remote Similarity	NPD4786	Approved
0.6977	Remote Similarity	NPD5328	Approved
0.6974	Remote Similarity	NPD7150	Approved
0.6974	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7152	Approved
0.6974	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7151	Approved
0.6951	Remote Similarity	NPD3667	Approved
0.6933	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8264	Approved
0.6914	Remote Similarity	NPD4748	Discontinued
0.6914	Remote Similarity	NPD7509	Discontinued
0.6842	Remote Similarity	NPD7143	Approved
0.6842	Remote Similarity	NPD7144	Approved
0.6835	Remote Similarity	NPD6117	Approved
0.68	Remote Similarity	NPD5360	Phase 3
0.68	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4195	Approved
0.675	Remote Similarity	NPD6932	Approved
0.675	Remote Similarity	NPD6116	Phase 1
0.6744	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4202	Approved
0.6711	Remote Similarity	NPD6923	Approved
0.6711	Remote Similarity	NPD6922	Approved
0.6709	Remote Similarity	NPD3703	Phase 2
0.6709	Remote Similarity	NPD4190	Phase 3
0.6709	Remote Similarity	NPD5275	Approved
0.6707	Remote Similarity	NPD6931	Approved
0.6707	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6629	Remote Similarity	NPD8035	Phase 2
0.6629	Remote Similarity	NPD8034	Phase 2
0.6623	Remote Similarity	NPD4789	Approved
0.6623	Remote Similarity	NPD4244	Approved
0.6623	Remote Similarity	NPD4245	Approved
0.6588	Remote Similarity	NPD3666	Approved
0.6588	Remote Similarity	NPD3665	Phase 1
0.6588	Remote Similarity	NPD3133	Approved
0.6585	Remote Similarity	NPD6929	Approved
0.6562	Remote Similarity	NPD385	Approved
0.6562	Remote Similarity	NPD384	Approved
0.6559	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7514	Phase 3
0.6506	Remote Similarity	NPD7332	Phase 2
0.6494	Remote Similarity	NPD3698	Phase 2
0.6489	Remote Similarity	NPD4696	Approved
0.6489	Remote Similarity	NPD5285	Approved
0.6489	Remote Similarity	NPD7639	Approved
0.6489	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD6695	Phase 3
0.6463	Remote Similarity	NPD7145	Approved
0.6452	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD7902	Approved
0.6437	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5223	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6683	Phase 2
0.6383	Remote Similarity	NPD5290	Discontinued
0.6354	Remote Similarity	NPD5211	Phase 2
0.6354	Remote Similarity	NPD5226	Approved
0.6354	Remote Similarity	NPD5225	Approved
0.6354	Remote Similarity	NPD5224	Approved
0.6354	Remote Similarity	NPD4633	Approved
0.6353	Remote Similarity	NPD4223	Phase 3
0.6353	Remote Similarity	NPD4221	Approved
0.6344	Remote Similarity	NPD4697	Phase 3
0.6341	Remote Similarity	NPD6925	Approved
0.6341	Remote Similarity	NPD5776	Phase 2
0.6329	Remote Similarity	NPD4758	Discontinued
0.6322	Remote Similarity	NPD6893	Approved
0.6322	Remote Similarity	NPD5329	Approved
0.6316	Remote Similarity	NPD4700	Approved
0.631	Remote Similarity	NPD6928	Phase 2
0.6289	Remote Similarity	NPD5174	Approved
0.6289	Remote Similarity	NPD5175	Approved
0.6265	Remote Similarity	NPD3671	Phase 1
0.625	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4623	Approved
0.6237	Remote Similarity	NPD4629	Approved
0.6237	Remote Similarity	NPD5210	Approved
0.6235	Remote Similarity	NPD6898	Phase 1
0.6235	Remote Similarity	NPD6902	Approved
0.6224	Remote Similarity	NPD5141	Approved
0.6216	Remote Similarity	NPD368	Approved
0.6207	Remote Similarity	NPD4197	Approved
0.6207	Remote Similarity	NPD3668	Phase 3
0.62	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6881	Approved
0.62	Remote Similarity	NPD6899	Approved
0.6196	Remote Similarity	NPD6399	Phase 3
0.618	Remote Similarity	NPD3573	Approved
0.618	Remote Similarity	NPD7524	Approved
0.618	Remote Similarity	NPD7750	Discontinued
0.6162	Remote Similarity	NPD7128	Approved
0.6162	Remote Similarity	NPD5739	Approved
0.6162	Remote Similarity	NPD6675	Approved
0.6162	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD388	Approved
0.6154	Remote Similarity	NPD6705	Phase 1
0.6154	Remote Similarity	NPD386	Approved
0.6129	Remote Similarity	NPD7900	Approved
0.6129	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4754	Approved
0.6118	Remote Similarity	NPD4695	Discontinued
0.6105	Remote Similarity	NPD6084	Phase 2
0.6105	Remote Similarity	NPD6083	Phase 2
0.6104	Remote Similarity	NPD4224	Phase 2
0.61	Remote Similarity	NPD5697	Approved
0.6078	Remote Similarity	NPD7102	Approved
0.6078	Remote Similarity	NPD6883	Approved
0.6078	Remote Similarity	NPD7290	Approved
0.6071	Remote Similarity	NPD5364	Discontinued
0.6071	Remote Similarity	NPD3617	Approved
0.6067	Remote Similarity	NPD5690	Phase 2
0.6067	Remote Similarity	NPD5279	Phase 3
0.6067	Remote Similarity	NPD4690	Approved
0.6067	Remote Similarity	NPD4138	Approved
0.6067	Remote Similarity	NPD4689	Approved
0.6067	Remote Similarity	NPD5205	Approved
0.6067	Remote Similarity	NPD4693	Phase 3
0.6067	Remote Similarity	NPD4688	Approved
0.6053	Remote Similarity	NPD371	Approved
0.6044	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6011	Approved
0.604	Remote Similarity	NPD4730	Approved
0.604	Remote Similarity	NPD4729	Approved
0.604	Remote Similarity	NPD7320	Approved
0.602	Remote Similarity	NPD7632	Discontinued
0.6019	Remote Similarity	NPD6847	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD8130	Phase 1
0.6019	Remote Similarity	NPD6649	Approved
0.6019	Remote Similarity	NPD6869	Approved
0.6019	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4768	Approved
0.598	Remote Similarity	NPD6014	Approved
0.598	Remote Similarity	NPD6373	Approved
0.598	Remote Similarity	NPD6372	Approved
0.598	Remote Similarity	NPD6012	Approved
0.598	Remote Similarity	NPD6013	Approved
0.5962	Remote Similarity	NPD6882	Approved
0.5962	Remote Similarity	NPD8297	Approved
0.5941	Remote Similarity	NPD5701	Approved
0.5934	Remote Similarity	NPD4722	Approved
0.5934	Remote Similarity	NPD4723	Approved
0.5934	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6081	Approved
0.5922	Remote Similarity	NPD5169	Approved
0.5922	Remote Similarity	NPD5248	Approved
0.5922	Remote Similarity	NPD5247	Approved
0.5922	Remote Similarity	NPD5249	Phase 3
0.5922	Remote Similarity	NPD4634	Approved
0.5922	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5250	Approved
0.5922	Remote Similarity	NPD5135	Approved
0.5922	Remote Similarity	NPD5251	Approved
0.5918	Remote Similarity	NPD4159	Approved
0.5914	Remote Similarity	NPD7087	Discontinued
0.5914	Remote Similarity	NPD6411	Approved
0.5904	Remote Similarity	NPD3702	Approved
0.5889	Remote Similarity	NPD7521	Approved
0.5889	Remote Similarity	NPD6409	Approved
0.5889	Remote Similarity	NPD5280	Approved
0.5889	Remote Similarity	NPD4694	Approved
0.5889	Remote Similarity	NPD5330	Approved
0.5889	Remote Similarity	NPD7334	Approved
0.5889	Remote Similarity	NPD7146	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