NPASS Compound

Structure

NPC195489 OpenBabel07101718232D 30 34 0 0 1 0 0 0 0 0999 V2000 -6.9047 3.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5665 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 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 -0.8660 -1.5000 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 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 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 -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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9266 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 1 0 0 0 21 24 1 0 0 0 0 22 28 1 6 0 0 0 23 30 1 6 0 0 0 24 26 1 6 0 0 0 25 27 1 1 0 0 0 25 29 1 0 0 0 0 26 27 1 6 0 0 0 27 6 1 1 0 0 0 28 29 1 1 0 0 0 29 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.37
Volume:	473.512
LogP:	7.156
LogD:	5.576
LogS:	-6.535
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	5.467
Fsp3:	0.931
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.854
MDCK Permeability:	1.1180247383890674e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	95.71968841552734%
Volume Distribution (VD):	1.234
Pgp-substrate:	1.890999674797058%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.235
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.121
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.738

ADMET: Excretion

Clearance (CL):	9.445
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.706
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.528
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.766
Skin Sensitization:	0.949
Carcinogencity:	0.333
Eye Corrosion:	0.528
Eye Irritation:	0.284
Respiratory Toxicity:	0.678

Download Data

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

Natural Product: NPC195489

Natural Product ID:	NPC195489
*Common Name:**	AIPIOTMFPXYEQS-ZQQHNXPESA-N
IUPAC Name:	n.a.
Synonyms:	24-Methylenepollinastanol
Standard InCHIKey:	AIPIOTMFPXYEQS-ZQQHNXPESA-N
Standard InCHI:	InChI=1S/C29H48O/c1-19(2)20(3)7-8-21(4)24-12-13-27(6)25-10-9-22-17-23(30)11-14-28(22)18-29(25,28)16-15-26(24,27)5/h19,21-25,30H,3,7-18H2,1-2,4-6H3/t21-,22+,23+,24-,25+,26-,27+,28-,29+/m1/s1
SMILES:	O[C@H]1CC[C@]23[C@H](C1)CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390965
PubChem CID:	14757096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO33305	musa sapientum	Species	Musaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	6

Activity Type	# Activity
Cell Line	1
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[512060]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[512060]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	30.5	%	PMID[512060]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	72.7	%	PMID[512060]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	95.8	%	PMID[512060]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	9.5	nM	PMID[512060]
NPT2	Others	Unspecified		Activity	=	1.5	n.a.	PMID[512060]

☑ 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 NPC195489 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	175
0.1-0.2	2470
0.2-0.3	14204
0.3-0.4	11550
0.4-0.5	5234
0.5-0.6	5403
0.6-0.7	2691
0.7-0.8	782
0.8-0.85	114
0.85-0.9	56
0.9-0.95	9
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9853	High Similarity	NPC145552
0.9853	High Similarity	NPC5046
0.9853	High Similarity	NPC196358
0.9853	High Similarity	NPC254509
0.9853	High Similarity	NPC49168
0.971	High Similarity	NPC230704
0.971	High Similarity	NPC70982
0.971	High Similarity	NPC200243
0.9559	High Similarity	NPC111234
0.9437	High Similarity	NPC331618
0.9437	High Similarity	NPC257191
0.9412	High Similarity	NPC45296
0.9306	High Similarity	NPC85346
0.9306	High Similarity	NPC65897
0.9306	High Similarity	NPC472342
0.9306	High Similarity	NPC302041
0.9286	High Similarity	NPC192638
0.9286	High Similarity	NPC25511
0.9286	High Similarity	NPC62657
0.9155	High Similarity	NPC212879
0.9155	High Similarity	NPC240235
0.9155	High Similarity	NPC185536
0.9155	High Similarity	NPC178383
0.9155	High Similarity	NPC104387
0.9155	High Similarity	NPC3403
0.9155	High Similarity	NPC231256
0.9041	High Similarity	NPC312328
0.9028	High Similarity	NPC14112
0.9028	High Similarity	NPC91573
0.9028	High Similarity	NPC78067
0.9028	High Similarity	NPC93662
0.9028	High Similarity	NPC237460
0.9028	High Similarity	NPC86305
0.9028	High Similarity	NPC278091
0.9014	High Similarity	NPC472503
0.9014	High Similarity	NPC308440
0.8955	High Similarity	NPC476737
0.8955	High Similarity	NPC27243
0.8904	High Similarity	NPC212241
0.8904	High Similarity	NPC202540
0.8904	High Similarity	NPC119355
0.8904	High Similarity	NPC34019
0.8904	High Similarity	NPC248830
0.8889	High Similarity	NPC103822
0.8889	High Similarity	NPC471723
0.8889	High Similarity	NPC257347
0.8889	High Similarity	NPC141071
0.8806	High Similarity	NPC69149
0.8784	High Similarity	NPC477817
0.8784	High Similarity	NPC6978
0.8784	High Similarity	NPC102708
0.8784	High Similarity	NPC138621
0.8784	High Similarity	NPC244385
0.8784	High Similarity	NPC285761
0.8784	High Similarity	NPC167037
0.8784	High Similarity	NPC301707
0.8784	High Similarity	NPC31828
0.8784	High Similarity	NPC477819
0.8784	High Similarity	NPC42853
0.8767	High Similarity	NPC189883
0.8767	High Similarity	NPC134330
0.8767	High Similarity	NPC38141
0.8767	High Similarity	NPC129165
0.875	High Similarity	NPC476736
0.8732	High Similarity	NPC164045
0.8701	High Similarity	NPC113978
0.8676	High Similarity	NPC41577
0.8676	High Similarity	NPC473276
0.8676	High Similarity	NPC474380
0.8667	High Similarity	NPC80530
0.8667	High Similarity	NPC49627
0.8667	High Similarity	NPC116119
0.8667	High Similarity	NPC273410
0.8667	High Similarity	NPC49599
0.8667	High Similarity	NPC472742
0.8667	High Similarity	NPC80297
0.8667	High Similarity	NPC475727
0.8649	High Similarity	NPC138502
0.8649	High Similarity	NPC307336
0.8649	High Similarity	NPC260301
0.863	High Similarity	NPC118508
0.863	High Similarity	NPC304309
0.863	High Similarity	NPC230301
0.863	High Similarity	NPC22105
0.863	High Similarity	NPC134847
0.863	High Similarity	NPC28657
0.863	High Similarity	NPC322353
0.863	High Similarity	NPC285893
0.863	High Similarity	NPC121744
0.863	High Similarity	NPC136188
0.863	High Similarity	NPC162742
0.863	High Similarity	NPC288035
0.8611	High Similarity	NPC472506
0.8553	High Similarity	NPC475679
0.8553	High Similarity	NPC71535
0.8553	High Similarity	NPC322313
0.8553	High Similarity	NPC236237
0.8553	High Similarity	NPC13554
0.8553	High Similarity	NPC102253
0.8553	High Similarity	NPC78545
0.8533	High Similarity	NPC472499
0.8533	High Similarity	NPC472500
0.8533	High Similarity	NPC472501
0.8514	High Similarity	NPC300324
0.8514	High Similarity	NPC470362
0.8514	High Similarity	NPC321381
0.8514	High Similarity	NPC202642
0.8514	High Similarity	NPC46160
0.8514	High Similarity	NPC107059
0.8514	High Similarity	NPC240604
0.8514	High Similarity	NPC321016
0.8514	High Similarity	NPC73875
0.8514	High Similarity	NPC113733
0.8507	High Similarity	NPC148174
0.8507	High Similarity	NPC218585
0.8507	High Similarity	NPC71460
0.8493	Intermediate Similarity	NPC469534
0.8493	Intermediate Similarity	NPC469533
0.8493	Intermediate Similarity	NPC469593
0.8481	Intermediate Similarity	NPC76518
0.8472	Intermediate Similarity	NPC301226
0.8462	Intermediate Similarity	NPC134481
0.8462	Intermediate Similarity	NPC82623
0.8429	Intermediate Similarity	NPC473230
0.8429	Intermediate Similarity	NPC475884
0.8421	Intermediate Similarity	NPC24504
0.8421	Intermediate Similarity	NPC1319
0.8421	Intermediate Similarity	NPC30986
0.8421	Intermediate Similarity	NPC209430
0.8421	Intermediate Similarity	NPC476316
0.84	Intermediate Similarity	NPC214570
0.84	Intermediate Similarity	NPC155986
0.84	Intermediate Similarity	NPC198968
0.84	Intermediate Similarity	NPC318495
0.8382	Intermediate Similarity	NPC114891
0.8375	Intermediate Similarity	NPC71520
0.8375	Intermediate Similarity	NPC269058
0.8356	Intermediate Similarity	NPC211009
0.8356	Intermediate Similarity	NPC201373
0.8354	Intermediate Similarity	NPC86238
0.8333	Intermediate Similarity	NPC477599
0.8333	Intermediate Similarity	NPC218616
0.8333	Intermediate Similarity	NPC296701
0.8333	Intermediate Similarity	NPC477858
0.8312	Intermediate Similarity	NPC47149
0.8312	Intermediate Similarity	NPC236112
0.8312	Intermediate Similarity	NPC206735
0.831	Intermediate Similarity	NPC160209
0.8289	Intermediate Similarity	NPC477522
0.8289	Intermediate Similarity	NPC474216
0.8289	Intermediate Similarity	NPC186191
0.8289	Intermediate Similarity	NPC76931
0.8289	Intermediate Similarity	NPC275910
0.8289	Intermediate Similarity	NPC475
0.8289	Intermediate Similarity	NPC307965
0.8289	Intermediate Similarity	NPC473943
0.8289	Intermediate Similarity	NPC472502
0.8289	Intermediate Similarity	NPC18603
0.8289	Intermediate Similarity	NPC205455
0.8289	Intermediate Similarity	NPC87604
0.8272	Intermediate Similarity	NPC89747
0.8267	Intermediate Similarity	NPC247325
0.8267	Intermediate Similarity	NPC244488
0.8261	Intermediate Similarity	NPC68656
0.825	Intermediate Similarity	NPC22133
0.8243	Intermediate Similarity	NPC100334
0.8228	Intermediate Similarity	NPC475726
0.8228	Intermediate Similarity	NPC110778
0.8228	Intermediate Similarity	NPC477818
0.8228	Intermediate Similarity	NPC5280
0.8228	Intermediate Similarity	NPC207013
0.8228	Intermediate Similarity	NPC246956
0.8228	Intermediate Similarity	NPC211135
0.8228	Intermediate Similarity	NPC85095
0.8228	Intermediate Similarity	NPC216420
0.8228	Intermediate Similarity	NPC470929
0.8228	Intermediate Similarity	NPC232023
0.8228	Intermediate Similarity	NPC472743
0.8205	Intermediate Similarity	NPC157655
0.8205	Intermediate Similarity	NPC474531
0.8194	Intermediate Similarity	NPC299948
0.8194	Intermediate Similarity	NPC210323
0.8194	Intermediate Similarity	NPC241085
0.8194	Intermediate Similarity	NPC470830
0.8182	Intermediate Similarity	NPC472463
0.8182	Intermediate Similarity	NPC84694
0.8182	Intermediate Similarity	NPC109546
0.8182	Intermediate Similarity	NPC143182
0.8182	Intermediate Similarity	NPC28862
0.8182	Intermediate Similarity	NPC47808
0.8182	Intermediate Similarity	NPC5604
0.8182	Intermediate Similarity	NPC47982
0.8182	Intermediate Similarity	NPC81306
0.8182	Intermediate Similarity	NPC155924
0.8182	Intermediate Similarity	NPC328714
0.8171	Intermediate Similarity	NPC146937
0.8171	Intermediate Similarity	NPC67872
0.8148	Intermediate Similarity	NPC94462
0.8133	Intermediate Similarity	NPC144075
0.8125	Intermediate Similarity	NPC474233

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 NPC195489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	2732
0.2-0.3	4411
0.3-0.4	1251
0.4-0.5	224
0.5-0.6	172
0.6-0.7	133
0.7-0.8	37
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.863	High Similarity	NPD6942	Approved
0.863	High Similarity	NPD7339	Approved
0.8553	High Similarity	NPD7525	Registered
0.8026	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6924	Approved
0.7763	Intermediate Similarity	NPD6926	Approved
0.7733	Intermediate Similarity	NPD7151	Approved
0.7733	Intermediate Similarity	NPD7152	Approved
0.7733	Intermediate Similarity	NPD7150	Approved
0.7733	Intermediate Similarity	NPD4243	Approved
0.7722	Intermediate Similarity	NPD7645	Phase 2
0.7703	Intermediate Similarity	NPD6923	Approved
0.7703	Intermediate Similarity	NPD6922	Approved
0.7703	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4786	Approved
0.76	Intermediate Similarity	NPD7144	Approved
0.76	Intermediate Similarity	NPD4787	Phase 1
0.76	Intermediate Similarity	NPD7143	Approved
0.7564	Intermediate Similarity	NPD6933	Approved
0.7561	Intermediate Similarity	NPD4788	Approved
0.7532	Intermediate Similarity	NPD4784	Approved
0.7532	Intermediate Similarity	NPD4785	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5328	Approved
0.7439	Intermediate Similarity	NPD3667	Approved
0.7407	Intermediate Similarity	NPD4748	Discontinued
0.7308	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3618	Phase 1
0.7284	Intermediate Similarity	NPD6929	Approved
0.7273	Intermediate Similarity	NPD6079	Approved
0.7273	Intermediate Similarity	NPD8034	Phase 2
0.7273	Intermediate Similarity	NPD8035	Phase 2
0.7237	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4190	Phase 3
0.7215	Intermediate Similarity	NPD5275	Approved
0.7209	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6931	Approved
0.7195	Intermediate Similarity	NPD6930	Phase 2
0.7195	Intermediate Similarity	NPD7509	Discontinued
0.7125	Intermediate Similarity	NPD6117	Approved
0.7108	Intermediate Similarity	NPD6902	Approved
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7059	Intermediate Similarity	NPD3666	Approved
0.7037	Intermediate Similarity	NPD6925	Approved
0.7037	Intermediate Similarity	NPD6116	Phase 1
0.7037	Intermediate Similarity	NPD6932	Approved
0.7037	Intermediate Similarity	NPD5776	Phase 2
0.7	Intermediate Similarity	NPD4202	Approved
0.6951	Remote Similarity	NPD6697	Approved
0.6951	Remote Similarity	NPD6118	Approved
0.6951	Remote Similarity	NPD6115	Approved
0.6951	Remote Similarity	NPD6114	Approved
0.6951	Remote Similarity	NPD7145	Approved
0.6941	Remote Similarity	NPD6695	Phase 3
0.6923	Remote Similarity	NPD4244	Approved
0.6923	Remote Similarity	NPD4789	Approved
0.6923	Remote Similarity	NPD4245	Approved
0.6883	Remote Similarity	NPD5360	Phase 3
0.6883	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6683	Phase 2
0.6867	Remote Similarity	NPD4195	Approved
0.686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6399	Phase 3
0.6809	Remote Similarity	NPD7638	Approved
0.6795	Remote Similarity	NPD3698	Phase 2
0.679	Remote Similarity	NPD3703	Phase 2
0.6786	Remote Similarity	NPD6928	Phase 2
0.6786	Remote Similarity	NPD7514	Phase 3
0.6782	Remote Similarity	NPD6893	Approved
0.6774	Remote Similarity	NPD4697	Phase 3
0.6774	Remote Similarity	NPD5221	Approved
0.6774	Remote Similarity	NPD5222	Approved
0.6774	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7640	Approved
0.6737	Remote Similarity	NPD7639	Approved
0.6711	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5279	Phase 3
0.6703	Remote Similarity	NPD7515	Phase 2
0.6702	Remote Similarity	NPD4755	Approved
0.6702	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3668	Phase 3
0.6629	Remote Similarity	NPD7524	Approved
0.6629	Remote Similarity	NPD7750	Discontinued
0.6628	Remote Similarity	NPD4221	Approved
0.6628	Remote Similarity	NPD4223	Phase 3
0.6591	Remote Similarity	NPD5329	Approved
0.6588	Remote Similarity	NPD7332	Phase 2
0.6585	Remote Similarity	NPD8264	Approved
0.6562	Remote Similarity	NPD5286	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.6562	Remote Similarity	NPD5285	Approved
0.6562	Remote Similarity	NPD4696	Approved
0.6548	Remote Similarity	NPD3671	Phase 1
0.6512	Remote Similarity	NPD6898	Phase 1
0.6495	Remote Similarity	NPD5223	Approved
0.6477	Remote Similarity	NPD4197	Approved
0.6458	Remote Similarity	NPD5290	Discontinued
0.6456	Remote Similarity	NPD6705	Phase 1
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.642	Remote Similarity	NPD4758	Discontinued
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.6383	Remote Similarity	NPD7748	Approved
0.6374	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD5174	Approved
0.6354	Remote Similarity	NPD6084	Phase 2
0.6354	Remote Similarity	NPD6083	Phase 2
0.6353	Remote Similarity	NPD3617	Approved
0.6344	Remote Similarity	NPD7087	Discontinued
0.6333	Remote Similarity	NPD7521	Approved
0.6333	Remote Similarity	NPD5205	Approved
0.6333	Remote Similarity	NPD4693	Phase 3
0.6333	Remote Similarity	NPD6684	Approved
0.6333	Remote Similarity	NPD5330	Approved
0.6333	Remote Similarity	NPD4138	Approved
0.6333	Remote Similarity	NPD7146	Approved
0.6333	Remote Similarity	NPD4688	Approved
0.6333	Remote Similarity	NPD6409	Approved
0.6333	Remote Similarity	NPD4690	Approved
0.6333	Remote Similarity	NPD7334	Approved
0.6333	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.6304	Remote Similarity	NPD6051	Approved
0.63	Remote Similarity	NPD5141	Approved
0.6275	Remote Similarity	NPD7320	Approved
0.6275	Remote Similarity	NPD6881	Approved
0.6275	Remote Similarity	NPD6899	Approved
0.6263	Remote Similarity	NPD7632	Discontinued
0.6238	Remote Similarity	NPD4768	Approved
0.6238	Remote Similarity	NPD4767	Approved
0.622	Remote Similarity	NPD6081	Approved
0.6214	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD6373	Approved
0.6203	Remote Similarity	NPD4224	Phase 2
0.6196	Remote Similarity	NPD4722	Approved
0.6196	Remote Similarity	NPD6672	Approved
0.6196	Remote Similarity	NPD4723	Approved
0.6196	Remote Similarity	NPD6903	Approved
0.6196	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD385	Approved
0.6176	Remote Similarity	NPD5697	Approved
0.6176	Remote Similarity	NPD384	Approved
0.6176	Remote Similarity	NPD5701	Approved
0.6163	Remote Similarity	NPD5364	Discontinued
0.6162	Remote Similarity	NPD4159	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD5280	Approved
0.6154	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5690	Phase 2
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD4694	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6146	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4139	Approved
0.6136	Remote Similarity	NPD4692	Approved
0.6117	Remote Similarity	NPD5168	Approved
0.6117	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD4729	Approved
0.6117	Remote Similarity	NPD4730	Approved
0.6117	Remote Similarity	NPD5128	Approved
0.6095	Remote Similarity	NPD6650	Approved
0.6095	Remote Similarity	NPD6617	Approved
0.6095	Remote Similarity	NPD8130	Phase 1
0.6095	Remote Similarity	NPD6649	Approved
0.6095	Remote Similarity	NPD6847	Approved
0.6095	Remote Similarity	NPD6869	Approved
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6700	Approved
0.6058	Remote Similarity	NPD6013	Approved
0.6058	Remote Similarity	NPD6014	Approved
0.6058	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD6882	Approved
0.6038	Remote Similarity	NPD8297	Approved
0.6024	Remote Similarity	NPD5777	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5135	Approved
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD6702	Approved
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD5169	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