NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	446.38
Volume:	499.648
LogP:	5.245
LogD:	4.98
LogS:	-4.94
# Rotatable Bonds:	6
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	4.99
Fsp3:	0.931
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:	-4.776
MDCK Permeability:	4.2160205339314416e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.749
Plasma Protein Binding (PPB):	92.27842712402344%
Volume Distribution (VD):	1.476
Pgp-substrate:	2.652419090270996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.398
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.83
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	17.582
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.81
Skin Sensitization:	0.228
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.587

Download Data

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

Natural Product: NPC477817

Natural Product ID:	NPC477817
*Common Name:**	17-(5-ethyl-6-methylhept-6-en-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,12,16-triol
IUPAC Name:	17-(5-ethyl-6-methylhept-6-en-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,12,16-triol
Synonyms:
Standard InCHIKey:	FMNHMKJQPJAHCG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H50O3/c1-7-19(17(2)3)9-8-18(4)27-25(31)15-24-22-11-10-20-14-21(30)12-13-28(20,5)23(22)16-26(32)29(24,27)6/h18-27,30-32H,2,7-16H2,1,3-6H3
SMILES:	CCC(CCC(C)C1C(CC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56676304
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO33580	Psammoclema sp.	Species	Chondropsidae	Eukaryota	n.a.	Nelson Bay, New South Wales, Australia (3243'0.5'' S, 15208'25.0'' E)	2006-OCT	PMID[19132863]

☑ 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
GI50	4
IC50	1

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	7100	nM	PMID[19132863]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	10000	nM	PMID[19132863]
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	11000	nM	PMID[19132863]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	13000	nM	PMID[19132863]
NPT2	Others	Unspecified		IC50	>	300000	nM	PMID[19132863]

☑ 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 NPC477817 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	177
0.1-0.2	2215
0.2-0.3	9849
0.3-0.4	14622
0.4-0.5	5726
0.5-0.6	4705
0.6-0.7	3830
0.7-0.8	1297
0.8-0.85	142
0.85-0.9	81
0.9-0.95	47
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477819
0.973	High Similarity	NPC78545
0.973	High Similarity	NPC71535
0.9595	High Similarity	NPC24504
0.9467	High Similarity	NPC47149
0.9459	High Similarity	NPC472502
0.9459	High Similarity	NPC472499
0.9459	High Similarity	NPC475
0.9459	High Similarity	NPC472500
0.9444	High Similarity	NPC472503
0.9444	High Similarity	NPC308440
0.9351	High Similarity	NPC232023
0.9351	High Similarity	NPC477818
0.9351	High Similarity	NPC110778
0.9333	High Similarity	NPC476316
0.9324	High Similarity	NPC138502
0.9324	High Similarity	NPC202540
0.9315	High Similarity	NPC3403
0.9231	High Similarity	NPC255882
0.9211	High Similarity	NPC475679
0.92	High Similarity	NPC42853
0.92	High Similarity	NPC31828
0.9189	High Similarity	NPC14112
0.9189	High Similarity	NPC38141
0.9189	High Similarity	NPC86305
0.9167	High Similarity	NPC111234
0.9103	High Similarity	NPC193870
0.9103	High Similarity	NPC141941
0.9079	High Similarity	NPC472742
0.9079	High Similarity	NPC116119
0.9079	High Similarity	NPC49599
0.9079	High Similarity	NPC49627
0.9079	High Similarity	NPC80297
0.9079	High Similarity	NPC475727
0.9067	High Similarity	NPC307336
0.9067	High Similarity	NPC260301
0.9054	High Similarity	NPC70982
0.9054	High Similarity	NPC104387
0.9054	High Similarity	NPC240235
0.9054	High Similarity	NPC185536
0.9054	High Similarity	NPC230704
0.9054	High Similarity	NPC231256
0.9054	High Similarity	NPC178383
0.9054	High Similarity	NPC103822
0.9054	High Similarity	NPC212879
0.9028	High Similarity	NPC45296
0.9	High Similarity	NPC201273
0.9	High Similarity	NPC121981
0.9	High Similarity	NPC24277
0.8987	High Similarity	NPC209802
0.8987	High Similarity	NPC475798
0.8987	High Similarity	NPC256567
0.8987	High Similarity	NPC127606
0.8987	High Similarity	NPC124172
0.8947	High Similarity	NPC167037
0.8947	High Similarity	NPC472501
0.8947	High Similarity	NPC301707
0.8947	High Similarity	NPC6978
0.8947	High Similarity	NPC138621
0.8947	High Similarity	NPC244385
0.8933	High Similarity	NPC93662
0.8933	High Similarity	NPC278091
0.8933	High Similarity	NPC91573
0.8933	High Similarity	NPC78067
0.8919	High Similarity	NPC145552
0.8919	High Similarity	NPC5046
0.8919	High Similarity	NPC196358
0.8919	High Similarity	NPC192638
0.8919	High Similarity	NPC49168
0.8919	High Similarity	NPC254509
0.8919	High Similarity	NPC62657
0.8919	High Similarity	NPC25511
0.8889	High Similarity	NPC477820
0.8861	High Similarity	NPC470929
0.8861	High Similarity	NPC216420
0.8861	High Similarity	NPC211135
0.8861	High Similarity	NPC85095
0.8846	High Similarity	NPC157655
0.8831	High Similarity	NPC80530
0.8831	High Similarity	NPC273410
0.8831	High Similarity	NPC1319
0.8831	High Similarity	NPC5604
0.8816	High Similarity	NPC212241
0.8816	High Similarity	NPC257191
0.8816	High Similarity	NPC248830
0.8816	High Similarity	NPC119355
0.8816	High Similarity	NPC331618
0.88	High Similarity	NPC200243
0.8784	High Similarity	NPC472506
0.8784	High Similarity	NPC195489
0.8767	High Similarity	NPC251201
0.8767	High Similarity	NPC232925
0.8767	High Similarity	NPC63588
0.8765	High Similarity	NPC139724
0.8765	High Similarity	NPC6605
0.875	High Similarity	NPC86238
0.8734	High Similarity	NPC470614
0.8734	High Similarity	NPC1272
0.8718	High Similarity	NPC26117
0.8718	High Similarity	NPC236237
0.8718	High Similarity	NPC102253
0.8718	High Similarity	NPC322313
0.8701	High Similarity	NPC285761
0.8701	High Similarity	NPC102708
0.8701	High Similarity	NPC472342
0.8684	High Similarity	NPC237460
0.8675	High Similarity	NPC105495
0.8667	High Similarity	NPC476736
0.8659	High Similarity	NPC474657
0.8659	High Similarity	NPC186145
0.8649	High Similarity	NPC164045
0.8625	High Similarity	NPC113978
0.859	High Similarity	NPC472463
0.8554	High Similarity	NPC470542
0.8554	High Similarity	NPC160304
0.8554	High Similarity	NPC475664
0.8533	High Similarity	NPC470610
0.85	High Similarity	NPC248886
0.85	High Similarity	NPC472504
0.8481	Intermediate Similarity	NPC13554
0.8472	Intermediate Similarity	NPC44122
0.8462	Intermediate Similarity	NPC65897
0.8462	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC477522
0.8462	Intermediate Similarity	NPC302041
0.8462	Intermediate Similarity	NPC85346
0.8452	Intermediate Similarity	NPC74258
0.8452	Intermediate Similarity	NPC109744
0.8442	Intermediate Similarity	NPC73875
0.8442	Intermediate Similarity	NPC189883
0.8421	Intermediate Similarity	NPC304499
0.8421	Intermediate Similarity	NPC48795
0.8395	Intermediate Similarity	NPC207013
0.8378	Intermediate Similarity	NPC66407
0.8375	Intermediate Similarity	NPC470383
0.8356	Intermediate Similarity	NPC253303
0.8356	Intermediate Similarity	NPC269077
0.8353	Intermediate Similarity	NPC53890
0.8353	Intermediate Similarity	NPC219937
0.8353	Intermediate Similarity	NPC475751
0.8353	Intermediate Similarity	NPC123252
0.8353	Intermediate Similarity	NPC473956
0.8353	Intermediate Similarity	NPC194485
0.8333	Intermediate Similarity	NPC300442
0.8333	Intermediate Similarity	NPC27243
0.8333	Intermediate Similarity	NPC476737
0.8333	Intermediate Similarity	NPC214570
0.8333	Intermediate Similarity	NPC473436
0.8313	Intermediate Similarity	NPC71520
0.8313	Intermediate Similarity	NPC269058
0.8312	Intermediate Similarity	NPC257347
0.8312	Intermediate Similarity	NPC141071
0.8312	Intermediate Similarity	NPC121744
0.8312	Intermediate Similarity	NPC317242
0.8312	Intermediate Similarity	NPC322353
0.8312	Intermediate Similarity	NPC471723
0.8312	Intermediate Similarity	NPC118508
0.8293	Intermediate Similarity	NPC299963
0.8293	Intermediate Similarity	NPC474493
0.8289	Intermediate Similarity	NPC211009
0.8289	Intermediate Similarity	NPC153719
0.8272	Intermediate Similarity	NPC296701
0.8272	Intermediate Similarity	NPC477599
0.8272	Intermediate Similarity	NPC20853
0.8272	Intermediate Similarity	NPC201852
0.8272	Intermediate Similarity	NPC218616
0.8256	Intermediate Similarity	NPC130840
0.825	Intermediate Similarity	NPC236112
0.825	Intermediate Similarity	NPC206735
0.8228	Intermediate Similarity	NPC312328
0.8228	Intermediate Similarity	NPC275910
0.8228	Intermediate Similarity	NPC477514
0.8214	Intermediate Similarity	NPC477600
0.8214	Intermediate Similarity	NPC271967
0.8205	Intermediate Similarity	NPC46160
0.8205	Intermediate Similarity	NPC107059
0.8205	Intermediate Similarity	NPC163597
0.8205	Intermediate Similarity	NPC300324
0.8205	Intermediate Similarity	NPC134330
0.8205	Intermediate Similarity	NPC240604
0.8205	Intermediate Similarity	NPC63958
0.8205	Intermediate Similarity	NPC321381
0.8205	Intermediate Similarity	NPC321016
0.8205	Intermediate Similarity	NPC202642
0.8205	Intermediate Similarity	NPC129165
0.8205	Intermediate Similarity	NPC96319
0.8194	Intermediate Similarity	NPC118937
0.8194	Intermediate Similarity	NPC167995
0.8194	Intermediate Similarity	NPC159654
0.8194	Intermediate Similarity	NPC281540
0.8193	Intermediate Similarity	NPC318390
0.8171	Intermediate Similarity	NPC246956
0.8171	Intermediate Similarity	NPC5280
0.8171	Intermediate Similarity	NPC472743
0.8171	Intermediate Similarity	NPC475726
0.8161	Intermediate Similarity	NPC26046
0.8158	Intermediate Similarity	NPC127094
0.8158	Intermediate Similarity	NPC1340
0.8158	Intermediate Similarity	NPC301226
0.8158	Intermediate Similarity	NPC187471

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 NPC477817 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2597
0.2-0.3	4296
0.3-0.4	1464
0.4-0.5	232
0.5-0.6	141
0.6-0.7	182
0.7-0.8	68
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD7525	Registered
0.8205	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7339	Approved
0.8077	Intermediate Similarity	NPD6942	Approved
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4787	Phase 1
0.7791	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4788	Approved
0.7692	Intermediate Similarity	NPD4243	Approved
0.7683	Intermediate Similarity	NPD7645	Phase 2
0.7662	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4748	Discontinued
0.759	Intermediate Similarity	NPD6928	Phase 2
0.7556	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD4785	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.75	Intermediate Similarity	NPD4784	Approved
0.747	Intermediate Similarity	NPD6929	Approved
0.7444	Intermediate Similarity	NPD8034	Phase 2
0.7444	Intermediate Similarity	NPD8035	Phase 2
0.7442	Intermediate Similarity	NPD4786	Approved
0.7416	Intermediate Similarity	NPD5328	Approved
0.7381	Intermediate Similarity	NPD6931	Approved
0.7381	Intermediate Similarity	NPD6930	Phase 2
0.7349	Intermediate Similarity	NPD6114	Approved
0.7349	Intermediate Similarity	NPD6697	Approved
0.7349	Intermediate Similarity	NPD6118	Approved
0.7349	Intermediate Similarity	NPD6115	Approved
0.734	Intermediate Similarity	NPD7638	Approved
0.7317	Intermediate Similarity	NPD6933	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7263	Intermediate Similarity	NPD7639	Approved
0.7263	Intermediate Similarity	NPD7640	Approved
0.7253	Intermediate Similarity	NPD6079	Approved
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7150	Approved
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7151	Approved
0.725	Intermediate Similarity	NPD7152	Approved
0.7241	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7234	Intermediate Similarity	NPD4755	Approved
0.7229	Intermediate Similarity	NPD6116	Phase 1
0.7229	Intermediate Similarity	NPD6932	Approved
0.7229	Intermediate Similarity	NPD5776	Phase 2
0.7229	Intermediate Similarity	NPD6925	Approved
0.7215	Intermediate Similarity	NPD6922	Approved
0.7215	Intermediate Similarity	NPD6923	Approved
0.7209	Intermediate Similarity	NPD3667	Approved
0.7195	Intermediate Similarity	NPD4190	Phase 3
0.7195	Intermediate Similarity	NPD3703	Phase 2
0.7195	Intermediate Similarity	NPD5275	Approved
0.7176	Intermediate Similarity	NPD7509	Discontinued
0.7143	Intermediate Similarity	NPD7145	Approved
0.7126	Intermediate Similarity	NPD6695	Phase 3
0.7125	Intermediate Similarity	NPD7144	Approved
0.7125	Intermediate Similarity	NPD7143	Approved
0.7125	Intermediate Similarity	NPD4245	Approved
0.7125	Intermediate Similarity	NPD4244	Approved
0.7108	Intermediate Similarity	NPD6117	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4195	Approved
0.7059	Intermediate Similarity	NPD6683	Phase 2
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD3698	Phase 2
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7514	Phase 3
0.6966	Remote Similarity	NPD6893	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6939	Remote Similarity	NPD4633	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6897	Remote Similarity	NPD6902	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6848	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD4221	Approved
0.6813	Remote Similarity	NPD7750	Discontinued
0.6813	Remote Similarity	NPD7524	Approved
0.6809	Remote Similarity	NPD6399	Phase 3
0.68	Remote Similarity	NPD5141	Approved
0.6796	Remote Similarity	NPD4634	Approved
0.6782	Remote Similarity	NPD7332	Phase 2
0.6778	Remote Similarity	NPD5329	Approved
0.6771	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7632	Discontinued
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6707	Remote Similarity	NPD4789	Approved
0.6705	Remote Similarity	NPD6898	Phase 1
0.6702	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD5173	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6632	Remote Similarity	NPD8171	Discontinued
0.6606	Remote Similarity	NPD7516	Approved
0.6604	Remote Similarity	NPD4632	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6559	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8294	Approved
0.6545	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6531	Remote Similarity	NPD6084	Phase 2
0.6531	Remote Similarity	NPD6083	Phase 2
0.6526	Remote Similarity	NPD7087	Discontinued
0.6522	Remote Similarity	NPD4689	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD4693	Phase 3
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD5205	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD4138	Approved
0.6522	Remote Similarity	NPD4688	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD4690	Approved
0.6522	Remote Similarity	NPD5279	Phase 3
0.6509	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6505	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5210	Approved
0.6495	Remote Similarity	NPD4629	Approved
0.6489	Remote Similarity	NPD6051	Approved
0.6486	Remote Similarity	NPD8033	Approved
0.6486	Remote Similarity	NPD8335	Approved
0.6486	Remote Similarity	NPD8378	Approved
0.6486	Remote Similarity	NPD8380	Approved
0.6486	Remote Similarity	NPD8296	Approved
0.6486	Remote Similarity	NPD8379	Approved
0.6484	Remote Similarity	NPD3668	Phase 3
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD5135	Approved
0.6465	Remote Similarity	NPD5290	Discontinued
0.6449	Remote Similarity	NPD8133	Approved
0.6422	Remote Similarity	NPD6009	Approved
0.6421	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6700	Approved
0.6415	Remote Similarity	NPD5216	Approved
0.6415	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD5217	Approved
0.6415	Remote Similarity	NPD5215	Approved
0.6408	Remote Similarity	NPD6008	Approved
0.6396	Remote Similarity	NPD6059	Approved
0.6396	Remote Similarity	NPD6054	Approved
0.6395	Remote Similarity	NPD8264	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6383	Remote Similarity	NPD6903	Approved
0.6383	Remote Similarity	NPD4722	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