NPASS Compound

Natural Product: NPC480938

Natural Product ID	NPC480938
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZCMUMJLYCIAMKY-UGMRTHNXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 100105 0 0 0 0 0 0 0 0999 V2000 -6.4007 -1.7728 -3.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3541 -1.1067 -1.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1135 -1.9152 -0.8178 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8377 0.3241 -1.9287 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8069 0.9702 -0.5943 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5752 0.7833 0.2191 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8168 -0.4606 -0.0474 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8695 -0.9783 -1.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3813 -0.3903 0.3666 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7963 -1.5438 0.6520 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3859 -1.7179 1.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6604 -0.4299 0.7657 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7988 -0.4855 1.0541 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1174 -1.2677 2.2954 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4565 -1.2702 -0.0941 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2647 -0.3653 -0.9881 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3656 0.3419 -0.2498 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8385 1.0275 1.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5640 0.6059 2.2208 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1207 2.5269 0.7996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3655 0.8862 1.0197 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6829 1.7129 2.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7263 1.9602 1.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4546 0.6662 1.3919 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0795 0.3017 2.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6366 0.8993 0.4496 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1486 1.2326 -0.9673 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4909 2.0504 0.8841 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7125 2.0113 0.0320 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0094 2.8852 -0.7558 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3486 -0.6102 0.0694 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5458 -0.3665 -0.5814 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6890 -0.1181 0.3776 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9703 -0.7261 -0.0999 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1609 -0.6105 -1.6012 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8820 -0.9707 -2.3333 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0777 -1.9774 -3.3806 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4024 -3.0350 -3.3630 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9865 -1.8395 -4.4247 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9195 -1.3927 -1.4466 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5786 0.6581 -1.9666 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0191 -2.0933 0.2107 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8270 1.2583 0.6130 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9813 0.8133 1.6390 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7811 -0.1758 2.3643 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5816 1.9375 2.1590 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8051 -2.7186 -3.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4382 -2.0918 -3.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9700 -1.1112 -3.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0087 -2.3755 -1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4619 -2.7465 -0.4747 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4540 -1.3766 0.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8989 0.2867 -2.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2346 0.8296 -2.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7165 0.6444 -0.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9776 2.0675 -0.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2814 -1.2652 0.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4233 -1.9687 -1.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4478 -0.3093 -2.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3657 -2.4892 0.5776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4557 -1.8874 2.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9539 -2.5950 0.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7444 -0.3314 -0.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5367 -2.2123 2.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9311 -0.7773 3.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1884 -1.6214 2.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6852 -1.7489 -0.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1125 -2.0661 0.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7655 -1.0456 -1.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6372 0.3129 -1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8401 1.0413 -0.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1645 -0.3159 1.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9683 0.4863 3.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3694 1.3529 2.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2571 3.0250 0.3153 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0659 2.6910 0.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1956 2.9623 1.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0173 1.3391 0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6253 1.2300 3.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1778 2.6958 2.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6580 2.5889 0.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2998 2.5539 2.3342 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2828 1.2754 3.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0558 -0.1818 2.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3943 -0.2413 3.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1247 1.6004 -0.9983 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2257 0.3320 -1.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7964 2.0044 -1.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9296 2.9770 0.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8389 1.9645 1.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4439 0.5458 -1.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4798 -0.5680 1.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8418 -0.2498 0.3811 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9575 -1.3276 -1.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4723 -0.0465 -2.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7524 -2.1320 -5.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8978 1.3047 -1.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8288 -2.4699 -0.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2878 1.8078 0.0103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6374 2.1185 3.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 2 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 36 40 1 0 35 41 1 0 34 42 1 0 33 43 1 0 6 44 1 1 44 45 2 0 44 46 1 0 8 2 1 0 26 9 1 0 40 32 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 7 57 1 1 8 58 1 0 8 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 12 63 1 6 14 64 1 0 14 65 1 0 14 66 1 0 15 67 1 0 15 68 1 0 16 69 1 0 16 70 1 0 17 71 1 6 19 72 1 0 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 20 77 1 0 21 78 1 6 22 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 25 83 1 0 25 84 1 0 25 85 1 0 27 86 1 0 27 87 1 0 27 88 1 0 28 89 1 0 28 90 1 0 32 91 1 6 33 92 1 1 34 93 1 1 35 94 1 6 36 95 1 6 39 96 1 0 41 97 1 0 42 98 1 0 43 99 1 0 46100 1 0 M END

Standard InCHIKey	ZCMUMJLYCIAMKY-UGMRTHNXSA-N
Standard InCHI	InChI=1S/C36H54O10/c1-31(2)14-15-36(30(43)44)19(16-31)18-8-9-21-33(5)12-11-23(45-29-26(40)24(38)25(39)27(46-29)28(41)42)32(3,4)20(33)10-13-34(21,6)35(18,7)17-22(36)37/h8,19-21,23-27,29,38-40H,9-17H2,1-7H3,(H,41,42)(H,43,44)/t19-,20-,21+,23-,24-,25-,26+,27-,29+,33-,34+,35+,36+/m0/s1
SMILES	CC1(C)CC[C@]2([C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.37	Volume:	657.23 ? Van der Waals volume.
Dense:	0.983	LogP:	2.933 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.666 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.689 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	35.0
TPSA:	170.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.426	Fsp³:	0.861
MCE-18:	133.104 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.967	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.175	Promiscuous compounds:	0.119

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.745	MDCK Permeability:	-5.152
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.37

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	84.043%	Volume Distribution (VD):	-0.627
Fu:	12.175% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.383	BCRP inhibitor:	0.0
BSEP inhibitor:	0.07

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.083	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.015 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.532

Half-life (T1/2):

2.212

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.633	Drug-induced Liver Injury (DILI):	0.942
AMES Toxicity:	0.394	Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.06	Skin Sensitization:	0.963
Carcinogencity:	0.451	Eye Corrosion:	0.0
Eye Irritation:	0.05	Respiratory Toxicity:	0.178
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.929
Hematotoxicity:	0.511	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.965	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.028
BCF:	0.475 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.546 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.018 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.237 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16926516]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[22834923]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30395460]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32569471]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065796]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23380	Camellia japonica	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23380	Camellia japonica	Species	Theaceae	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	Organism Name	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
Activity	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT804	Cell line	HT-22	Mus musculus	Activity	=	72.0	%	PMID[32569471]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC480938 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18638
0.1-0.2	26928
0.2-0.3	3286
0.3-0.4	696
0.4-0.5	247
0.5-0.6	43
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7976	Intermediate Similarity	NPC286347
0.7111	Intermediate Similarity	NPC294112
0.7111	Intermediate Similarity	NPC480937
0.7033	Intermediate Similarity	NPC480943
0.6893	Remote Similarity	NPC480939
0.6263	Remote Similarity	NPC114441
0.62	Remote Similarity	NPC472949
0.62	Remote Similarity	NPC6377
0.62	Remote Similarity	NPC208381
0.6196	Remote Similarity	NPC283849
0.6196	Remote Similarity	NPC606107
0.6064	Remote Similarity	NPC31839
0.604	Remote Similarity	NPC157868
0.6	Remote Similarity	NPC309780
0.6	Remote Similarity	NPC242611
0.5825	Remote Similarity	NPC22956
0.5729	Remote Similarity	NPC224121
0.5657	Remote Similarity	NPC482752
0.5619	Remote Similarity	NPC75417
0.5579	Remote Similarity	NPC204407
0.5545	Remote Similarity	NPC164194
0.5521	Remote Similarity	NPC28198
0.5521	Remote Similarity	NPC476123
0.551	Remote Similarity	NPC100383
0.5444	Remote Similarity	NPC488521
0.5429	Remote Similarity	NPC473884
0.5429	Remote Similarity	NPC488516
0.5385	Remote Similarity	NPC25605
0.5385	Remote Similarity	NPC56713
0.537	Remote Similarity	NPC180550
0.537	Remote Similarity	NPC35405
0.5333	Remote Similarity	NPC127056
0.5333	Remote Similarity	NPC109079
0.5333	Remote Similarity	NPC482748
0.5327	Remote Similarity	NPC242840
0.5327	Remote Similarity	NPC469945
0.5294	Remote Similarity	NPC475472
0.5283	Remote Similarity	NPC488561
0.5281	Remote Similarity	NPC120840
0.5234	Remote Similarity	NPC482746
0.5234	Remote Similarity	NPC80843
0.5234	Remote Similarity	NPC475171
0.5229	Remote Similarity	NPC104400
0.5229	Remote Similarity	NPC10320
0.5138	Remote Similarity	NPC114304
0.513	Remote Similarity	NPC480936
0.5106	Remote Similarity	NPC601365
0.5098	Remote Similarity	NPC284807
0.5096	Remote Similarity	NPC270667
0.5093	Remote Similarity	NPC482747
0.5093	Remote Similarity	NPC202666
0.5093	Remote Similarity	NPC471961
0.5093	Remote Similarity	NPC242015
0.5091	Remote Similarity	NPC251768
0.5091	Remote Similarity	NPC159309
0.5091	Remote Similarity	NPC86222
0.5089	Remote Similarity	NPC488515
0.5049	Remote Similarity	NPC191410

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC480938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6003
0.1-0.2	3085
0.2-0.3	53
0.3-0.4	7
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
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
0.5093	Remote Similarity	NPD8328	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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